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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1047.
Published online 2009 April 18. doi:  10.1107/S160053680901174X
PMCID: PMC2977729

(E)-2-Hydroxy­naphthalene-1-carb­al­de­hyde semicarbazone

Abstract

The title compound, C12H11N3O2, adopts an E or trans configuration with respect to the C=N bond. There is an intra­molecular O—H(...)N hydrogen bond involving the hydroxyl H atom and an N atom of the hydrazine group. In the crystal structure, mol­ecules are connected via N—H(...)O hydrogen bonds, forming a three-dimensional network.

Related literature

For the potential pharmacological and anti­tumor properties of hydrazones and Schiff bases, see: Karthikeyan et al. (2006 [triangle]); Khattab (2005 [triangle]); Kucukguzel et al. (2006 [triangle]). For related structures, see: Okabe et al. (1993 [triangle]); Zhang et al. (1999 [triangle]); Xu et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1047-scheme1.jpg

Experimental

Crystal data

  • C12H11N3O2
  • M r = 229.24
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1047-efi1.jpg
  • a = 16.091 (3) Å
  • b = 4.7350 (9) Å
  • c = 15.776 (3) Å
  • β = 114.26 (3)°
  • V = 1095.8 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 283 K
  • 0.20 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.988, T max = 0.989
  • 6629 measured reflections
  • 2324 independent reflections
  • 1550 reflections with I > 2σ(I)
  • R int = 0.015

Refinement

  • R[F 2 > 2σ(F 2)] = 0.037
  • wR(F 2) = 0.107
  • S = 1.05
  • 2324 reflections
  • 155 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.15 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [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: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680901174X/su2105sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901174X/su2105Isup2.hkl

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

Acknowledgments

This work was supported by the Key Project of Science and Technology of Anhui, People’s Republic of China (grant No. 08010302218).

supplementary crystallographic information

Comment

Hydrazones and Schiff bases have attracted much attention for their excellent biological properties, especially for their potential pharmacological and antitumor properties (Kucukguzel et al., 2006; Khattab, 2005; Karthikeyan et al., 2006; Okabe et al., 1993). As we are interested in this field of research (Xu et al. 2009), we report herein on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1 and geometrical parameters are given in the archived CIF. The molecule has a trans configuration about the C=N bond. There is an intramolecular O-H···N hydrogen bond involving the naphthalene hydroxyl sunstituent and atom N1 of the hydrazine group (Table 1).

In the crystal structure symmetry related molecules are connected via N-H···O hydrogen bonds so forming a three-dimensional structure (Table 1 and Fig. 2).

Experimental

The ligand H2L was prepared according to the reported procedure (Zhang et al., 1999). A solution of semicarbazide hydrochloride (0.112 g, 1 mmol) in 5 ml of ethanol was added slowly to a solution of 2-hydro-1- naphthaldehyde (0.172 g,1 mmol) in 15 ml absolute ethanol, under heating and stirring. The mixture was refluxed for 3 h, then cooled to rt and left to stand in air for 5 days. Yellow block-shaped crystals were formed on slow evaporation of the solvent.

Refinement

All the H-atoms were placed in calculated positions [O—H = 0.82 Å, N—H = 0.86 Å, C—H = 0.93 Å] and treated as riding [Uiso(H) = 1.5Ueq(parent O-atom) and = 1.2Ueq(parent C-atom and N-atom)].

Figures

Fig. 1.
The molecular structure of the title compound, showing 30% probability displacement ellipsoids (H-atoms have been omitted for clarity).
Fig. 2.
Crystal packing of the title compound viewed along the b axis. The intra- and intermolecular hydrogen bonds are shown as dashed lines (details are given in Table 1).

Crystal data

C12H11N3O2F(000) = 480
Mr = 229.24Dx = 1.389 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 628 reflections
a = 16.091 (3) Åθ = 2.5–15°
b = 4.7350 (9) ŵ = 0.10 mm1
c = 15.776 (3) ÅT = 283 K
β = 114.26 (3)°Block, yellow
V = 1095.8 (4) Å30.20 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2324 independent reflections
Radiation source: fine-focus sealed tube1550 reflections with I > 2σ(I)
graphiteRint = 0.015
[var phi] and ω scansθmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −20→20
Tmin = 0.988, Tmax = 0.989k = −6→4
6629 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0607P)2] where P = (Fo2 + 2Fc2)/3
2324 reflections(Δ/σ)max < 0.001
155 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.15 e Å3

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
C10.23742 (8)0.2085 (3)0.15396 (8)0.0367 (3)
C20.24256 (9)0.1120 (3)0.23930 (9)0.0441 (3)
C30.30716 (10)−0.0898 (3)0.29109 (10)0.0538 (4)
H3C0.3094−0.14970.34810.065*
C40.36618 (10)−0.1978 (3)0.25859 (10)0.0530 (4)
H4A0.4089−0.33070.29390.064*
C50.36419 (8)−0.1126 (3)0.17185 (9)0.0435 (3)
C60.42499 (10)−0.2280 (3)0.13721 (11)0.0572 (4)
H6A0.4674−0.36220.17220.069*
C70.42258 (10)−0.1462 (4)0.05361 (12)0.0623 (4)
H7A0.4634−0.22310.03200.075*
C80.35881 (11)0.0531 (3)0.00052 (11)0.0571 (4)
H8A0.35720.1088−0.05670.068*
C90.29852 (9)0.1678 (3)0.03161 (9)0.0477 (4)
H9A0.25600.2989−0.00530.057*
C100.29938 (8)0.0915 (3)0.11853 (9)0.0377 (3)
C110.17325 (8)0.4299 (3)0.10430 (9)0.0383 (3)
H110.17770.51850.05370.046*
C12−0.01922 (9)0.7854 (3)0.10281 (9)0.0405 (3)
N10.11062 (7)0.5029 (2)0.13008 (7)0.0419 (3)
N20.05492 (7)0.7251 (2)0.08591 (7)0.0447 (3)
H20.06710.82660.04730.054*
N3−0.04085 (8)0.6020 (3)0.15536 (8)0.0551 (4)
H3A−0.08730.63330.16780.066*
H3B−0.00830.45300.17650.066*
O10.18694 (7)0.2086 (2)0.27791 (7)0.0616 (3)
H10.15210.32720.24360.092*
O2−0.06341 (7)1.00232 (19)0.07058 (6)0.0510 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0325 (6)0.0356 (7)0.0400 (7)−0.0004 (5)0.0127 (6)0.0012 (6)
C20.0426 (7)0.0456 (8)0.0445 (7)0.0005 (6)0.0183 (6)0.0036 (6)
C30.0547 (9)0.0555 (9)0.0458 (8)0.0047 (7)0.0151 (7)0.0146 (7)
C40.0425 (8)0.0467 (9)0.0575 (9)0.0073 (7)0.0080 (7)0.0094 (7)
C50.0317 (7)0.0378 (8)0.0543 (8)−0.0019 (6)0.0108 (6)−0.0042 (6)
C60.0386 (8)0.0501 (9)0.0765 (11)0.0066 (7)0.0172 (7)−0.0063 (8)
C70.0479 (8)0.0625 (11)0.0841 (12)0.0004 (8)0.0347 (8)−0.0223 (9)
C80.0560 (9)0.0636 (10)0.0593 (9)−0.0035 (8)0.0313 (8)−0.0097 (8)
C90.0436 (8)0.0519 (9)0.0478 (8)0.0035 (6)0.0191 (7)−0.0028 (6)
C100.0313 (6)0.0356 (7)0.0438 (7)−0.0040 (5)0.0131 (6)−0.0052 (6)
C110.0371 (7)0.0381 (8)0.0389 (7)−0.0001 (6)0.0150 (6)0.0004 (6)
C120.0416 (7)0.0368 (8)0.0434 (7)0.0014 (6)0.0177 (6)−0.0071 (6)
N10.0385 (6)0.0396 (6)0.0480 (6)0.0057 (5)0.0182 (5)0.0030 (5)
N20.0428 (6)0.0401 (7)0.0560 (7)0.0097 (5)0.0250 (6)0.0108 (5)
N30.0579 (8)0.0484 (8)0.0733 (8)0.0123 (6)0.0414 (7)0.0112 (6)
O10.0642 (7)0.0759 (8)0.0575 (6)0.0184 (6)0.0378 (6)0.0190 (5)
O20.0525 (6)0.0432 (6)0.0616 (6)0.0139 (5)0.0280 (5)0.0039 (5)

Geometric parameters (Å, °)

C1—C21.3916 (17)C8—C91.3667 (18)
C1—C101.4390 (16)C8—H8A0.9300
C1—C111.4540 (17)C9—C101.4126 (18)
C2—O11.3525 (15)C9—H9A0.9300
C2—C31.4013 (19)C11—N11.2798 (15)
C3—C41.352 (2)C11—H110.9300
C3—H3C0.9300C12—O21.2336 (14)
C4—C51.414 (2)C12—N31.3417 (16)
C4—H4A0.9300C12—N21.3554 (15)
C5—C61.4120 (19)N1—N21.3719 (14)
C5—C101.4172 (18)N2—H20.8600
C6—C71.360 (2)N3—H3A0.8600
C6—H6A0.9300N3—H3B0.8600
C7—C81.392 (2)O1—H10.8200
C7—H7A0.9300
C2—C1—C10118.31 (12)C9—C8—H8A119.7
C2—C1—C11120.31 (11)C7—C8—H8A119.7
C10—C1—C11121.34 (11)C8—C9—C10121.44 (14)
O1—C2—C1122.52 (12)C8—C9—H9A119.3
O1—C2—C3115.95 (12)C10—C9—H9A119.3
C1—C2—C3121.53 (12)C9—C10—C5117.51 (11)
C4—C3—C2120.36 (13)C9—C10—C1123.13 (12)
C4—C3—H3C119.8C5—C10—C1119.36 (11)
C2—C3—H3C119.8N1—C11—C1120.08 (11)
C3—C4—C5121.27 (13)N1—C11—H11120.0
C3—C4—H4A119.4C1—C11—H11120.0
C5—C4—H4A119.4O2—C12—N3122.80 (12)
C6—C5—C4121.35 (14)O2—C12—N2119.96 (12)
C6—C5—C10119.48 (13)N3—C12—N2117.24 (12)
C4—C5—C10119.17 (12)C11—N1—N2118.76 (10)
C7—C6—C5121.13 (15)C12—N2—N1120.39 (10)
C7—C6—H6A119.4C12—N2—H2119.8
C5—C6—H6A119.4N1—N2—H2119.8
C6—C7—C8119.79 (13)C12—N3—H3A120.0
C6—C7—H7A120.1C12—N3—H3B120.0
C8—C7—H7A120.1H3A—N3—H3B120.0
C9—C8—C7120.64 (14)C2—O1—H1109.5
C10—C1—C2—O1−179.71 (12)C8—C9—C10—C1179.65 (12)
C11—C1—C2—O12.7 (2)C6—C5—C10—C90.63 (18)
C10—C1—C2—C31.2 (2)C4—C5—C10—C9−179.00 (12)
C11—C1—C2—C3−176.41 (13)C6—C5—C10—C1179.93 (12)
O1—C2—C3—C4−179.60 (13)C4—C5—C10—C10.30 (18)
C1—C2—C3—C4−0.4 (2)C2—C1—C10—C9178.15 (12)
C2—C3—C4—C5−0.4 (2)C11—C1—C10—C9−4.27 (19)
C3—C4—C5—C6−179.15 (13)C2—C1—C10—C5−1.10 (18)
C3—C4—C5—C100.5 (2)C11—C1—C10—C5176.48 (11)
C4—C5—C6—C7179.75 (13)C2—C1—C11—N1−12.17 (19)
C10—C5—C6—C70.1 (2)C10—C1—C11—N1170.30 (11)
C5—C6—C7—C8−0.5 (2)C1—C11—N1—N2175.68 (11)
C6—C7—C8—C90.0 (2)O2—C12—N2—N1172.35 (11)
C7—C8—C9—C100.8 (2)N3—C12—N2—N1−7.35 (18)
C8—C9—C10—C5−1.1 (2)C11—N1—N2—C12171.46 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.832.5563 (15)146
N2—H2···O2i0.862.012.8385 (15)163
N3—H3A···O1ii0.862.142.9871 (15)171
N3—H3B···O2iii0.862.633.0957 (16)115

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2105).

References

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  • Khattab, S. N. (2005). Molecules, 10, 1218–1228. [PubMed]
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  • Okabe, N., Nakamura, T. & Fukuda, H. (1993). Acta Cryst. C49, 1678–1680.
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