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ISSN: 2056-9890

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

aDepartment of Materials Science and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China
*Correspondence e-mail: tsuhgf@163.com

(Received 26 November 2010; accepted 2 December 2010; online 8 December 2010)

In the title compound, C15H12ClN5O, the mean planes of the benzotriazole and chloro­phenyl fragments form a dihedral angle of 70.8 (1)°. In the crystal, mol­ecules are linked into infinite chains along the a axis by N—H⋯O hydrogen bonds. Weak inter­molecular C—H⋯N hydrogen bonds further link these chains into layers parallel to the ab plane. The crystal studied was a racemic twin.

Related literature

For related structures, see: Shi et al. (2007a[Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007a). Acta Cryst. E63, o4561.],b[Shi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007b). Acta Cryst. E63, o4642.]); Ji & Shi (2008[Ji, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o2141.]).

[Scheme 1]

Experimental

Crystal data
  • C15H12ClN5O

  • Mr = 313.75

  • Monoclinic, P 21

  • a = 4.6777 (16) Å

  • b = 11.726 (4) Å

  • c = 13.328 (5) Å

  • β = 94.224 (7)°

  • V = 729.0 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.27 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, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.968, Tmax = 0.979

  • 3851 measured reflections

  • 1902 independent reflections

  • 1370 reflections with I > 2σ(I)

  • Rint = 0.039

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.089

  • S = 1.01

  • 1902 reflections

  • 199 parameters

  • H-atom parameters constrained

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.17 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 544 Flack pairs

  • Flack parameter: 0.55 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N4—H4⋯O1i 0.86 2.04 2.841 (4) 154
C7—H7A⋯N3ii 0.97 2.48 3.320 (6) 145
Symmetry codes: (i) x+1, y, z; (ii) [-x+2, y+{\script{1\over 2}}, -z].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

In continuation of our structural studies of benzotriazole derivatives (Shi et al., 2007a,b; Ji et al., 2008), herewith we present the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and in a good agreement with those observed in the related compounds (Shi et al., 2007a,b; Ji et al., 2008). The mean planes of the benzotriazole and chlorophenyl fragments form a dihedral angle of 70.8 (1)°.

In the crystal structure, the molecules are linked into infinite chains along the a axis by N—H···O hydrogen bonds (Table 1; Fig. 2). Weak intermolecular C—H···N hydrogen bonds (Table 1) link further these chains into layers parallel to ab plane.

Related literature top

For related structures, see: Shi et al. (2007a,b); Ji et al. (2008).

Experimental top

The title compound was synthesized by the reaction of 2-(1H-1,2,3-benzotriazol-1-yl)acetohydrazide (1 mmol, 191.2 mg) with 2-chlorobenzaldehyde(1 mmol, 140.6 mg) in ethanol(20 ml)under reflux conditions (348 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days colourless crystals suitable for X-ray diffraction study were obtained.

Refinement top

All H atoms were placed in idealized positions (C—H = 0.93— 0.97 Å, N—H = 0.86 Å) and refined as riding atoms. For those bound to C, Uiso(H) = 1.2 or 1.5Ueq(C). while for those bound to N, Uiso(H) = 1.2 Ueq(N).

Structure description top

In continuation of our structural studies of benzotriazole derivatives (Shi et al., 2007a,b; Ji et al., 2008), herewith we present the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles are normal and in a good agreement with those observed in the related compounds (Shi et al., 2007a,b; Ji et al., 2008). The mean planes of the benzotriazole and chlorophenyl fragments form a dihedral angle of 70.8 (1)°.

In the crystal structure, the molecules are linked into infinite chains along the a axis by N—H···O hydrogen bonds (Table 1; Fig. 2). Weak intermolecular C—H···N hydrogen bonds (Table 1) link further these chains into layers parallel to ab plane.

For related structures, see: Shi et al. (2007a,b); Ji et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 30% probability level.
[Figure 2] Fig. 2. Hydrogen-bonded (dashed lines) chain in (I). H atoms not included in hydrogen bonding have been omitted for clarity.
2-(1H-1,2,3-Benzotriazol-1-yl)-N'-(2- chlorobenzylidene)acetohydrazide top
Crystal data top
C15H12ClN5OF(000) = 324
Mr = 313.75Dx = 1.429 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 676 reflections
a = 4.6777 (16) Åθ = 2.3–18.9°
b = 11.726 (4) ŵ = 0.27 mm1
c = 13.328 (5) ÅT = 295 K
β = 94.224 (7)°Block, colourless
V = 729.0 (4) Å30.12 × 0.10 × 0.08 mm
Z = 2
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1902 independent reflections
Radiation source: fine-focus sealed tube1370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.039
phi and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 55
Tmin = 0.968, Tmax = 0.979k = 913
3851 measured reflectionsl = 1514
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.089 w = 1/[σ2(Fo2) + (0.0267P)2 + 0.1806P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
1902 reflectionsΔρmax = 0.16 e Å3
199 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), 544 Flack pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.55 (11)
Crystal data top
C15H12ClN5OV = 729.0 (4) Å3
Mr = 313.75Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.6777 (16) ŵ = 0.27 mm1
b = 11.726 (4) ÅT = 295 K
c = 13.328 (5) Å0.12 × 0.10 × 0.08 mm
β = 94.224 (7)°
Data collection top
Bruker APEXII CCD area-detector
diffractometer
1902 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
1370 reflections with I > 2σ(I)
Tmin = 0.968, Tmax = 0.979Rint = 0.039
3851 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.16 e Å3
S = 1.01Δρmin = 0.17 e Å3
1902 reflectionsAbsolute structure: Flack (1983), 544 Flack pairs
199 parametersAbsolute structure parameter: 0.55 (11)
0 restraints
Special details top

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) top
xyzUiso*/Ueq
Cl11.5224 (3)0.95422 (11)0.46424 (9)0.0660 (4)
O10.7318 (6)0.5815 (3)0.17718 (18)0.0473 (8)
N10.9309 (7)0.4707 (3)0.0172 (2)0.0377 (8)
N20.9247 (9)0.3561 (3)0.0325 (3)0.0523 (10)
N30.7297 (9)0.3113 (3)0.0307 (3)0.0561 (11)
N41.1772 (7)0.6360 (3)0.2368 (2)0.0413 (9)
H41.35550.64120.22570.050*
N51.0786 (8)0.6779 (3)0.3252 (2)0.0391 (9)
C10.7313 (9)0.5002 (4)0.0583 (3)0.0361 (10)
C20.6509 (10)0.6045 (4)0.1011 (3)0.0466 (11)
H20.73860.67260.08050.056*
C30.4329 (11)0.6000 (5)0.1759 (3)0.0619 (14)
H30.36920.66770.20630.074*
C40.3028 (11)0.4976 (6)0.2083 (3)0.0632 (15)
H4A0.15860.49960.26020.076*
C50.3809 (10)0.3947 (5)0.1661 (3)0.0585 (14)
H50.29310.32690.18740.070*
C60.6035 (10)0.3978 (4)0.0881 (3)0.0437 (11)
C71.1297 (9)0.5398 (4)0.0782 (3)0.0427 (11)
H7A1.19550.60240.03830.051*
H7B1.29500.49430.10110.051*
C80.9886 (9)0.5868 (4)0.1684 (3)0.0354 (9)
C91.2636 (10)0.7317 (3)0.3822 (3)0.0421 (11)
H91.44510.74690.36120.050*
C101.1839 (9)0.7691 (4)0.4815 (3)0.0406 (10)
C111.2939 (9)0.8682 (4)0.5275 (3)0.0446 (11)
C121.2219 (10)0.8998 (4)0.6219 (3)0.0564 (13)
H121.29750.96600.65160.068*
C131.0391 (12)0.8333 (5)0.6715 (3)0.0608 (15)
H130.99240.85440.73550.073*
C140.9219 (11)0.7351 (4)0.6283 (3)0.0569 (14)
H140.79530.69080.66230.068*
C150.9967 (10)0.7035 (4)0.5332 (3)0.0481 (12)
H150.91980.63740.50380.058*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0682 (8)0.0536 (7)0.0772 (8)0.0105 (7)0.0128 (7)0.0064 (7)
O10.0283 (18)0.071 (2)0.0436 (17)0.0008 (16)0.0071 (13)0.0112 (15)
N10.042 (2)0.032 (2)0.0409 (19)0.0015 (18)0.0082 (16)0.0021 (16)
N20.063 (3)0.038 (2)0.057 (2)0.001 (2)0.010 (2)0.001 (2)
N30.071 (3)0.038 (2)0.059 (2)0.006 (2)0.005 (2)0.006 (2)
N40.033 (2)0.055 (2)0.0374 (19)0.0000 (18)0.0100 (16)0.0138 (17)
N50.038 (2)0.047 (2)0.033 (2)0.0031 (18)0.0092 (17)0.0054 (17)
C10.035 (3)0.039 (2)0.036 (2)0.000 (2)0.0133 (19)0.0049 (19)
C20.051 (3)0.041 (3)0.049 (3)0.003 (2)0.014 (2)0.002 (2)
C30.058 (4)0.075 (4)0.053 (3)0.014 (3)0.005 (3)0.009 (3)
C40.051 (3)0.096 (5)0.042 (3)0.007 (3)0.004 (2)0.006 (3)
C50.051 (3)0.079 (4)0.046 (3)0.012 (3)0.006 (2)0.020 (3)
C60.053 (3)0.040 (3)0.040 (2)0.002 (2)0.014 (2)0.009 (2)
C70.043 (3)0.052 (3)0.035 (2)0.006 (2)0.012 (2)0.009 (2)
C80.039 (3)0.037 (2)0.030 (2)0.001 (2)0.0049 (19)0.0016 (18)
C90.041 (3)0.046 (3)0.040 (2)0.004 (2)0.006 (2)0.007 (2)
C100.044 (3)0.046 (3)0.032 (2)0.008 (2)0.002 (2)0.0024 (19)
C110.044 (3)0.046 (3)0.044 (2)0.004 (2)0.002 (2)0.003 (2)
C120.067 (3)0.054 (3)0.048 (3)0.008 (3)0.001 (2)0.016 (2)
C130.077 (4)0.071 (4)0.035 (3)0.023 (3)0.010 (3)0.007 (3)
C140.068 (4)0.063 (3)0.042 (3)0.010 (3)0.017 (2)0.002 (2)
C150.051 (3)0.049 (3)0.044 (3)0.003 (2)0.005 (2)0.004 (2)
Geometric parameters (Å, º) top
Cl1—C111.733 (4)C4—H4A0.9300
O1—C81.217 (4)C5—C61.416 (6)
N1—N21.359 (5)C5—H50.9300
N1—C11.366 (5)C7—C81.517 (5)
N1—C71.440 (5)C7—H7A0.9700
N2—N31.306 (5)C7—H7B0.9700
N3—C61.377 (5)C9—C101.468 (5)
N4—C81.350 (5)C9—H90.9300
N4—N51.387 (4)C10—C151.386 (6)
N4—H40.8600C10—C111.394 (5)
N5—C91.275 (5)C11—C121.377 (5)
C1—C61.387 (5)C12—C131.364 (6)
C1—C21.389 (6)C12—H120.9300
C2—C31.374 (6)C13—C141.383 (7)
C2—H20.9300C13—H130.9300
C3—C41.399 (7)C14—C151.390 (6)
C3—H30.9300C14—H140.9300
C4—C51.370 (7)C15—H150.9300
N2—N1—C1109.9 (4)C8—C7—H7A109.5
N2—N1—C7119.5 (4)N1—C7—H7B109.5
C1—N1—C7130.6 (3)C8—C7—H7B109.5
N3—N2—N1108.8 (4)H7A—C7—H7B108.1
N2—N3—C6108.2 (3)O1—C8—N4123.9 (4)
C8—N4—N5118.9 (3)O1—C8—C7123.2 (4)
C8—N4—H4120.5N4—C8—C7112.9 (4)
N5—N4—H4120.5N5—C9—C10118.5 (4)
C9—N5—N4115.3 (3)N5—C9—H9120.7
N1—C1—C6104.4 (3)C10—C9—H9120.7
N1—C1—C2132.5 (4)C15—C10—C11118.0 (3)
C6—C1—C2123.1 (4)C15—C10—C9119.6 (4)
C3—C2—C1115.4 (5)C11—C10—C9122.4 (4)
C3—C2—H2122.3C12—C11—C10121.3 (4)
C1—C2—H2122.3C12—C11—Cl1119.3 (4)
C2—C3—C4122.6 (5)C10—C11—Cl1119.5 (3)
C2—C3—H3118.7C13—C12—C11119.6 (4)
C4—C3—H3118.7C13—C12—H12120.2
C5—C4—C3122.2 (5)C11—C12—H12120.2
C5—C4—H4A118.9C12—C13—C14121.2 (4)
C3—C4—H4A118.9C12—C13—H13119.4
C4—C5—C6116.0 (5)C14—C13—H13119.4
C4—C5—H5122.0C13—C14—C15118.8 (5)
C6—C5—H5122.0C13—C14—H14120.6
N3—C6—C1108.7 (4)C15—C14—H14120.6
N3—C6—C5130.6 (4)C10—C15—C14121.1 (4)
C1—C6—C5120.7 (4)C10—C15—H15119.4
N1—C7—C8110.6 (3)C14—C15—H15119.4
N1—C7—H7A109.5
C1—N1—N2—N30.4 (4)N2—N1—C7—C893.6 (4)
C7—N1—N2—N3179.9 (3)C1—N1—C7—C885.8 (5)
N1—N2—N3—C60.5 (5)N5—N4—C8—O13.6 (6)
C8—N4—N5—C9174.3 (4)N5—N4—C8—C7177.1 (3)
N2—N1—C1—C60.1 (4)N1—C7—C8—O111.3 (6)
C7—N1—C1—C6179.6 (4)N1—C7—C8—N4169.5 (3)
N2—N1—C1—C2179.1 (4)N4—N5—C9—C10174.2 (3)
C7—N1—C1—C20.4 (7)N5—C9—C10—C1533.0 (6)
N1—C1—C2—C3178.9 (4)N5—C9—C10—C11148.1 (4)
C6—C1—C2—C30.2 (6)C15—C10—C11—C120.7 (6)
C1—C2—C3—C41.0 (6)C9—C10—C11—C12178.2 (4)
C2—C3—C4—C51.2 (8)C15—C10—C11—Cl1178.6 (3)
C3—C4—C5—C60.5 (7)C9—C10—C11—Cl12.6 (6)
N2—N3—C6—C10.5 (5)C10—C11—C12—C130.2 (7)
N2—N3—C6—C5179.5 (4)Cl1—C11—C12—C13179.1 (4)
N1—C1—C6—N30.2 (4)C11—C12—C13—C140.7 (7)
C2—C1—C6—N3179.5 (4)C12—C13—C14—C150.9 (7)
N1—C1—C6—C5179.7 (3)C11—C10—C15—C140.4 (6)
C2—C1—C6—C50.4 (6)C9—C10—C15—C14178.5 (4)
C4—C5—C6—N3179.7 (5)C13—C14—C15—C100.4 (7)
C4—C5—C6—C10.2 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.862.042.841 (4)154
C7—H7A···N3ii0.972.483.320 (6)145
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC15H12ClN5O
Mr313.75
Crystal system, space groupMonoclinic, P21
Temperature (K)295
a, b, c (Å)4.6777 (16), 11.726 (4), 13.328 (5)
β (°) 94.224 (7)
V3)729.0 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.12 × 0.10 × 0.08
Data collection
DiffractometerBruker APEXII CCD area-detector
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.968, 0.979
No. of measured, independent and
observed [I > 2σ(I)] reflections
3851, 1902, 1370
Rint0.039
(sin θ/λ)max1)0.596
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.089, 1.01
No. of reflections1902
No. of parameters199
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.16, 0.17
Absolute structureFlack (1983), 544 Flack pairs
Absolute structure parameter0.55 (11)

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4···O1i0.862.042.841 (4)154.0
C7—H7A···N3ii0.972.483.320 (6)145.3
Symmetry codes: (i) x+1, y, z; (ii) x+2, y+1/2, z.
 

Acknowledgements

This work was supported by Taian City Science and Technology Bureau (grant No. 20081009).

References

First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationJi, N.-N. & Shi, Z.-Q. (2008). Acta Cryst. E64, o2141.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationShi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007a). Acta Cryst. E63, o4561.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationShi, Z.-Q., Ji, N.-N., Zheng, Z.-B. & Li, J.-K. (2007b). Acta Cryst. E63, o4642.  Web of Science CSD CrossRef IUCr Journals Google Scholar

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