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Acta Crystallogr Sect E Struct Rep Online. 2008 April 1; 64(Pt 4): o655.
Published online 2008 March 5. doi:  10.1107/S1600536808005631
PMCID: PMC2961015

2-(1H-1,2,3-Benzotriazol-1-yl)-N′-cyclo­pentyl­ideneacetohydrazide

Abstract

The title compound, C13H15N5O, was synthesized by the reaction of 2-(1H-1,2,3-benzotriazol-1-yl)acetohydrazide with cyclo­penta­none. In the cyclopentane ring, two C atoms and their attached H atoms are disordered over two positions; the site occupancy factors are ca 0.63 and 0.37. In the crystal structure, mol­ecules are linked into infinite chains directed along the b axis by N—H(...)O hydrogen bonds. In addition, there are weak C—H(...)O and C—H(...)N hydrogen bonds, as well as C—H(...)π-ring inter­actions in the structure.

Related literature

For related literature, see: Allen (2002 [triangle]); Allen et al. (1987 [triangle]); Garnovskii et al. (1993 [triangle]); Anderson et al. (1997 [triangle]); Müller et al. (2006 [triangle]); Musie et al. (2001 [triangle]); Xu et al. (2002 [triangle]); Ghosh et al. (2002 [triangle]); Shi et al. (2007 [triangle]); Yang (2006 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o655-scheme1.jpg

Experimental

Crystal data

  • C13H15N5O
  • M r = 257.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o655-efi1.jpg
  • a = 11.926 (3) Å
  • b = 9.126 (2) Å
  • c = 12.095 (3) Å
  • β = 93.174 (5)°
  • V = 1314.4 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 295 (2) K
  • 0.32 × 0.24 × 0.11 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.990
  • 6723 measured reflections
  • 2323 independent reflections
  • 1114 reflections with I > 2σ(I)
  • R int = 0.065

Refinement

  • R[F 2 > 2σ(F 2)] = 0.059
  • wR(F 2) = 0.170
  • S = 1.01
  • 2323 reflections
  • 173 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.26 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SMART; data reduction: SAINT (Siemens, 1996 [triangle]); 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/S1600536808005631/fb2083sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808005631/fb2083Isup2.hkl

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

Acknowledgments

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y06-2-08).

supplementary crystallographic information

Comment

Recently, a number of Schiff-bases have been investigated because of their interesting coordination chemistry (Garnovskii et al., 1993; Musie et al., 2001; Ghosh et al., 2002; Shi et al., 2007) as well as due to their importance in biological systems (Anderson et al., 1997). The Schiff-bases containing the triazole group have attracted much attention because they exhibit potential bioactivities (Xu et al., 2002). In order to search for new triazole compounds with higher bioactivity, the title compound was synthesized and its crystal structure determined (Fig. 1 and Fig. 2). The bond lengths and angles are in good agreement with the expected values (Allen et al., 1987). In the crystal structure, the molecules are linked into infinite chains by the N—H···O hydrogen bonds. In addition, there are also present weak C—H···O and C—H···N hydrogen bonds as well as C—H···π-ring interactions (Tab. 1). Cg1 and Cg2 are the centroids pertinent to the rings N1\N2\N3\C1\C2 and C1\C2\···C6, respectively.

Experimental

The title compound was synthesized by the reaction of 2-(1H-1,2,3-benzotriazol-1-yl)acetohydrazide (1 mmol, 191.2 mg) with cyclopentanone (1 mmol, 84.1 mg) in ethanol (25 ml). The mixture was refluxed at 338 K for 4 h until a clear solution occurred. After ten days, colourless block crystals with approx. size 0.3 × 0.2 × 0.1 mm suitable for X-ray diffraction study were obtained. Yield, 257.3 mg, 87%. m. p. 490–492 K.

Analysis calculated for C13H15N5O: C 60.69, H 5.88, N 27.22%; found: C 60.66, H 5.82, N 27.17%.

Refinement

The majority of the H atoms could have been determined in the difference Fourier maps with exception of the disordered atoms C11, C11', C12 and C12'. During the refinement the H atoms were situated into idealized positions, constrained and refined as riding atoms. The constraints: Caryl—H = 0.93; Cmethylene—H = 0.97 Å, N—H = 0.86 Å; Uiso(H) = 1.2 Ueq(carrier atom). The disorder was treated with the following constraints and restraints: The anisotropic displacement parameters of the pairs of the atoms C11, C11' and C12, C12' were set equal by the command EADP (Sheldrick, 2008). The corresponding interatomic distances C11—C12 and C11'-C12' were restrained to 1.485 (10) Å while the distances C10—C11, C10—C11', C12—C13, C12'-C13 were restrained to 1.520 (10) Å. (The values of these distances were excerpted from the Cambridge Crystal Structure Database (Allen, 2002) for the structures that contained the similar fragment –N?cyclopentane as it is contained in the title structure. The searched structures were without disorder, errors and with R-factor < 0.05. 4 structures with the following REFCODES were found: HULJON, KERWUA, NAQSAZ and RAKHUH.) In addition, for the disordered parts the restrain SAME has been applied (Müller et al., 2006; Sheldrick, 2008). The respective occupancies were refined to 0.628 (9) and to 0.372 (9).

Figures

Fig. 1.
The molecular structure of the title compound with the displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
The crystal structure of the title compounds showing the infinite chains interconnected via the H—H···O hydrogen bonds. The dashed lines indicate the hydrogen bonds.

Crystal data

C13H15N5OF000 = 544
Mr = 257.30Dx = 1.300 Mg m3
Monoclinic, P21/cMelting point = 490–492 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71073 Å
a = 11.926 (3) ÅCell parameters from 526 reflections
b = 9.126 (2) Åθ = 2.8–19.1º
c = 12.095 (3) ŵ = 0.09 mm1
β = 93.174 (5)ºT = 295 (2) K
V = 1314.4 (5) Å3Block, colorless
Z = 40.32 × 0.24 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer2323 independent reflections
Radiation source: fine-focus sealed tube1114 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.065
T = 295(2) Kθmax = 25.1º
[var phi] and ω scansθmin = 1.7º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −14→14
Tmin = 0.972, Tmax = 0.990k = −10→10
6723 measured reflectionsl = −8→14

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)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.170H-atom parameters constrained
S = 1.01  w = 1/[σ2(Fo2) + (0.071P)2] where P = (Fo2 + 2Fc2)/3
2323 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.17 e Å3
7 restraintsΔρmin = −0.26 e Å3
74 constraintsExtinction correction: none

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*/UeqOcc. (<1)
O10.45566 (18)−0.0903 (2)0.2935 (2)0.0720 (8)
N10.2040 (3)0.0346 (3)0.4948 (3)0.0758 (10)
N20.3131 (3)0.0413 (3)0.4947 (2)0.0687 (9)
N30.3419 (2)0.1243 (3)0.4072 (2)0.0525 (7)
N40.55577 (19)0.0916 (3)0.2198 (2)0.0533 (8)
H40.58280.17850.22870.064*
N50.5824 (2)0.0084 (3)0.1280 (2)0.0589 (8)
C10.2485 (3)0.1717 (3)0.3495 (3)0.0502 (9)
C20.1608 (3)0.1146 (4)0.4060 (3)0.0603 (10)
C30.0492 (3)0.1441 (5)0.3729 (4)0.0807 (12)
H3−0.01030.10540.40990.097*
C40.0325 (3)0.2335 (5)0.2823 (4)0.0862 (13)
H4A−0.04070.25690.25790.103*
C50.1217 (3)0.2910 (4)0.2253 (3)0.0779 (12)
H50.10610.35110.16430.094*
C60.2317 (3)0.2607 (4)0.2572 (3)0.0613 (10)
H60.29120.29780.21920.074*
C70.4582 (2)0.1429 (3)0.3833 (3)0.0534 (9)
H7A0.50550.12610.44990.064*
H7B0.47060.24250.35870.064*
C80.4891 (2)0.0361 (3)0.2940 (3)0.0493 (8)
C90.6663 (3)0.0541 (3)0.0777 (3)0.0529 (9)
C100.7449 (3)0.1752 (4)0.1090 (3)0.0871 (13)
H10A0.77010.16830.18650.104*
H10B0.70940.26970.09590.104*
C130.7025 (3)−0.0176 (4)−0.0264 (3)0.0703 (11)
H13A0.7280−0.1170−0.01160.084*
H13B0.6409−0.0203−0.08230.084*
C110.8426 (3)0.1542 (4)0.0347 (3)0.116 (2)0.628 (9)
H11A0.87250.24790.01260.139*0.628 (9)
H11B0.90220.09820.07250.139*0.628 (9)
C120.7939 (3)0.0729 (4)−0.0628 (3)0.122 (4)0.628 (9)
H12A0.76590.1412−0.11930.147*0.628 (9)
H12B0.85080.0119−0.09390.147*0.628 (9)
C11'0.8241 (12)0.1710 (16)0.0129 (13)0.116 (2)0.372 (9)
H11C0.79580.2337−0.04710.139*0.372 (9)
H11D0.89850.20440.03760.139*0.372 (9)
C12'0.8279 (9)0.0159 (18)−0.0244 (18)0.122 (4)0.372 (9)
H12C0.8707−0.04540.02800.147*0.372 (9)
H12D0.85760.0068−0.09710.147*0.372 (9)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0847 (17)0.0349 (13)0.100 (2)−0.0061 (12)0.0413 (15)−0.0016 (12)
N10.081 (2)0.061 (2)0.090 (3)0.0051 (17)0.037 (2)0.0106 (19)
N20.080 (2)0.0599 (19)0.068 (2)0.0112 (16)0.0267 (17)0.0135 (16)
N30.0573 (17)0.0441 (16)0.0577 (18)0.0037 (14)0.0164 (15)0.0029 (14)
N40.0522 (16)0.0376 (15)0.072 (2)−0.0079 (12)0.0153 (15)−0.0014 (14)
N50.0638 (19)0.0484 (17)0.0662 (19)−0.0058 (14)0.0187 (16)−0.0038 (15)
C10.050 (2)0.048 (2)0.054 (2)0.0047 (16)0.0128 (18)−0.0080 (19)
C20.059 (2)0.053 (2)0.071 (3)0.0009 (19)0.023 (2)−0.009 (2)
C30.061 (3)0.089 (3)0.095 (3)−0.009 (2)0.029 (2)−0.020 (3)
C40.050 (2)0.123 (4)0.086 (3)0.003 (2)0.006 (2)−0.021 (3)
C50.071 (3)0.096 (3)0.066 (3)0.014 (2)0.005 (2)0.003 (2)
C60.060 (2)0.068 (2)0.056 (2)0.0048 (19)0.0079 (19)−0.002 (2)
C70.053 (2)0.0397 (18)0.069 (2)0.0004 (16)0.0123 (17)0.0030 (18)
C80.0459 (19)0.0354 (18)0.068 (2)0.0037 (15)0.0118 (17)0.0063 (17)
C90.051 (2)0.048 (2)0.061 (2)0.0030 (16)0.0114 (18)0.0065 (18)
C100.075 (3)0.073 (3)0.117 (4)−0.026 (2)0.042 (3)−0.015 (2)
C130.069 (2)0.073 (3)0.071 (3)−0.001 (2)0.015 (2)−0.004 (2)
C110.090 (4)0.104 (4)0.159 (6)−0.037 (3)0.068 (4)−0.032 (4)
C120.105 (5)0.148 (9)0.119 (8)−0.039 (5)0.058 (5)−0.038 (7)
C11'0.090 (4)0.104 (4)0.159 (6)−0.037 (3)0.068 (4)−0.032 (4)
C12'0.105 (5)0.148 (9)0.119 (8)−0.039 (5)0.058 (5)−0.038 (7)

Geometric parameters (Å, °)

O1—C81.220 (3)C7—H7B0.9700
N1—N21.302 (4)C9—C101.484 (4)
N1—C21.375 (4)C9—C131.503 (4)
N2—N31.361 (3)C10—C111.522 (4)
N3—C11.352 (4)C10—C11'1.538 (8)
N3—C71.443 (3)C10—H10A0.9700
N4—C81.332 (3)C10—H10B0.9700
N4—N51.397 (3)C13—C121.4555
N4—H40.8604C13—C12'1.526 (9)
N5—C91.270 (4)C13—H13A0.9700
C1—C21.383 (4)C13—H13B0.9700
C1—C61.387 (4)C11—C121.4841
C2—C31.395 (5)C11—H11A0.9700
C3—C41.372 (5)C11—H11B0.9700
C3—H30.9300C12—H12A0.9700
C4—C51.401 (5)C12—H12B0.9700
C4—H4A0.9300C11'—C12'1.487 (9)
C5—C61.374 (5)C11'—H11C0.9700
C5—H50.9300C11'—H11D0.9700
C6—H60.9300C12'—H12C0.9700
C7—C81.516 (4)C12'—H12D0.9700
C7—H7A0.9700
N2—N1—C2107.8 (3)C9—C10—C11'101.2 (6)
N1—N2—N3108.8 (3)C9—C10—H10A110.9
C1—N3—N2110.1 (3)C11—C10—H10A110.9
C1—N3—C7129.2 (3)C11'—C10—H10A123.9
N2—N3—C7120.6 (3)C9—C10—H10B110.9
C8—N4—N5120.0 (3)C11—C10—H10B110.9
C8—N4—H4120.0C11'—C10—H10B100.3
N5—N4—H4120.0H10A—C10—H10B108.9
C9—N5—N4115.0 (3)C12—C13—C9105.08 (18)
N3—C1—C2104.4 (3)C9—C13—C12'103.0 (7)
N3—C1—C6133.0 (3)C12—C13—H13A110.7
C2—C1—C6122.6 (3)C9—C13—H13A110.7
N1—C2—C1109.0 (3)C12'—C13—H13A83.5
N1—C2—C3129.6 (4)C12—C13—H13B110.7
C1—C2—C3121.4 (4)C9—C13—H13B110.7
C4—C3—C2116.0 (4)C12'—C13—H13B136.0
C4—C3—H3122.0H13A—C13—H13B108.8
C2—C3—H3122.0C12—C11—C10104.7 (2)
C3—C4—C5122.3 (4)C12—C11—H11A110.8
C3—C4—H4A118.9C10—C11—H11A111.0
C5—C4—H4A118.9C12—C11—H11B110.8
C6—C5—C4121.7 (4)C10—C11—H11B110.7
C6—C5—H5119.1H11A—C11—H11B108.9
C4—C5—H5119.1C13—C12—C11108.1
C5—C6—C1115.9 (3)C13—C12—H12A110.1
C5—C6—H6122.0C11—C12—H12A110.1
C1—C6—H6122.0C13—C12—H12B110.1
N3—C7—C8110.0 (2)C11—C12—H12B110.1
N3—C7—H7A109.7H12A—C12—H12B108.4
C8—C7—H7A109.7C12'—C11'—C10106.4 (10)
N3—C7—H7B109.7C12'—C11'—H11C110.4
C8—C7—H7B109.7C10—C11'—H11C110.4
H7A—C7—H7B108.2C12'—C11'—H11D110.4
O1—C8—N4124.3 (3)C10—C11'—H11D110.4
O1—C8—C7121.3 (3)H11C—C11'—H11D108.6
N4—C8—C7114.4 (3)C11'—C12'—C1398.6 (10)
N5—C9—C10128.7 (3)C11'—C12'—H12C112.1
N5—C9—C13121.9 (3)C11'—C12'—H12D112.1
C10—C9—C13109.4 (3)C13—C12'—H12D112.1
C9—C10—C11104.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.862.172.910 (3)144
C7—H7B···O1i0.972.583.435 (4)147
C7—H7B···N5i0.972.513.372 (4)147
C13—H13A···Cg1ii0.972.793.729 (4)163
C12'—H12C···Cg2ii0.972.993.820 (19)145

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FB2083).

References

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