2-(1H-Benzotriazol-1-yl)-N-(2-hydroxy­benzyl­idene)acetohydrazide

Shi, Z.-Q.; Ji, N.-N.; Zheng, Z.-B.; Li, J.-K.

doi:10.1107/S1600536807056206

2-(1H-Benzotriazol-1-yl)-N-(2-hydroxybenzylidene)acetohydrazide

Z.-Q. Shi, N.-N. Ji, Z.-B. Zheng and J.-K. Li

The title compound, C₁₅H₁₃N₅O₂, was synthesized by the reaction of 2-(1H-benzotriazol-1-yl)acetohydrazide with 2-hydroxybenzaldehyde. In the crystal structure, molecules are linked into infinite chains by N—H

N hydrogen bonds. There is also an intramolecular O—H

N hydrogen bond.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056206/cf2170sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056206/cf2170Isup2.hkl Contains datablock I

CCDC reference: 672894

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.009 Å
R factor = 0.045
wR factor = 0.095
Data-to-parameter ratio = 6.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) .....       6.42
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.05
           From the CIF: _reflns_number_total               1291
           Count of symmetry unique reflns         1296
           Completeness (_total/calc)             99.61%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Recently, a number of Schiff bases have been investigated in terms of their coordination chemistry (Garnovski et al., 1993; Musie et al., 2001; Paul et al., 2002; Yang, 2006) and biological applications (Anderson et al., 1997). Schiff bases containing the triazole group have attracted much interest because their potential bioactivities (Xu et al., 2002). In order to search for new triazole compounds with higher bioactivity, the title compound, (I), was synthesized and its crystal structure determined. In (I) (Fig. 1), the bond lengths are in good agreement with the expected values (Allen et al., 1987). The dihedral angle formed by the triazole ring and the 2-hydroxybenzylidene group is 78.99 (2)°. In the crystal structure (Fig. 2), the molecules are linked into infinite chains by N—H···N hydrogen bonds. There is also an intramolecular O—H···N hydrogen bond.

Related literature top

For related literature, see: Allen et al. (1987); Anderson et al. (1997); Garnovski et al. (1993); Musie et al. (2001); Paul et al. (2002); Xu et al. (2002); Yang (2006).

Experimental top

The title compound was synthesized by the reaction of 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetohydrazide (1 mmol, 191.2 mg) with 2-hydroxybenzaldehyde (1 mmol, 122.1 mg) in ethanol (20 ml) under reflux conditions (348 K) for 2 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days colorless crystals suitable for X-ray diffraction study were obtained. Yield, 248.1 mg, 84%. m.p. 239–241 K.

Analysis calculated for C₁₅H₁₃N₅O₂: C 61.01, H 4.44, N 23.72%; found: C 60.58, H 4.48, N 23.68%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The structure of the infinite chains formed via hydrogen bonds (dashed lines). H atoms have been omitted for clarity.

2-(1H-Benzotriazol-1-yl)-N'-(2-hydroxybenzylidene)acetohydrazide top

Crystal data top

C₁₅H₁₃N₅O₂	F(000) = 308
M_r = 295.30	D_x = 1.350 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 328 reflections
a = 10.644 (3) Å	θ = 2.9–15.7°
b = 4.4834 (12) Å	µ = 0.10 mm⁻¹
c = 15.807 (4) Å	T = 298 K
β = 105.672 (6)°	Block, colorless
V = 726.3 (3) Å³	0.14 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	1291 independent reflections
Radiation source: fine-focus sealed tube	752 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.987, T_max = 0.991	k = −5→5
3578 measured reflections	l = −18→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0348P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1291 reflections	Δρ_max = 0.13 e Å⁻³
201 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (3)

Crystal data top

C₁₅H₁₃N₅O₂	V = 726.3 (3) Å³
M_r = 295.30	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 10.644 (3) Å	µ = 0.10 mm⁻¹
b = 4.4834 (12) Å	T = 298 K
c = 15.807 (4) Å	0.14 × 0.12 × 0.10 mm
β = 105.672 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1291 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	752 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.991	R_int = 0.061
3578 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.095	H-atom parameters constrained
S = 1.00	Δρ_max = 0.13 e Å⁻³
1291 reflections	Δρ_min = −0.15 e Å⁻³
201 parameters

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

	x	y	z	U_iso*/U_eq
O1	1.2445 (4)	0.3630 (10)	0.8367 (3)	0.0847 (14)
H1	1.1824	0.2477	0.8248	0.127*
O2	0.8341 (4)	−0.4778 (9)	0.7704 (2)	0.0702 (12)
N1	1.0742 (4)	−0.0033 (9)	0.7359 (3)	0.0506 (12)
N2	0.9753 (4)	−0.2095 (9)	0.7182 (2)	0.0543 (12)
H2	0.9487	−0.2873	0.6667	0.065*
N3	0.9099 (4)	−0.2348 (9)	0.9340 (3)	0.0538 (12)
N4	0.9687 (4)	−0.4372 (10)	0.9947 (3)	0.0570 (12)
N5	0.8977 (4)	−0.4742 (10)	1.0501 (3)	0.0555 (12)
C1	1.2886 (6)	0.4036 (12)	0.7645 (4)	0.0625 (16)
C2	1.2334 (5)	0.2633 (11)	0.6851 (4)	0.0532 (14)
C3	1.2857 (6)	0.3228 (14)	0.6156 (4)	0.078 (2)
H3	1.2493	0.2328	0.5616	0.093*
C4	1.3899 (7)	0.5109 (15)	0.6246 (6)	0.091 (2)
H4	1.4241	0.5459	0.5773	0.109*
C5	1.4441 (7)	0.6491 (15)	0.7048 (6)	0.097 (2)
H5	1.5152	0.7761	0.7114	0.117*
C6	1.3929 (7)	0.5985 (14)	0.7742 (5)	0.088 (2)
H6	1.4279	0.6943	0.8276	0.105*
C7	1.1280 (5)	0.0542 (11)	0.6743 (3)	0.0509 (14)
H7	1.0977	−0.0431	0.6207	0.061*
C8	0.9199 (6)	−0.2896 (12)	0.7823 (3)	0.0515 (14)
C9	0.9742 (6)	−0.1365 (12)	0.8690 (3)	0.0614 (16)
H9A	1.0668	−0.1778	0.8900	0.074*
H9B	0.9633	0.0774	0.8610	0.074*
C10	0.7975 (5)	−0.1396 (11)	0.9496 (3)	0.0489 (14)
C11	0.7912 (5)	−0.2888 (12)	1.0249 (3)	0.0498 (14)
C12	0.6873 (6)	−0.2467 (13)	1.0622 (4)	0.0640 (16)
H12	0.6822	−0.3468	1.1127	0.077*
C13	0.5944 (6)	−0.0500 (14)	1.0198 (4)	0.0745 (18)
H13	0.5244	−0.0122	1.0430	0.089*
C14	0.5995 (6)	0.0970 (13)	0.9435 (4)	0.0768 (19)
H14	0.5313	0.2234	0.9161	0.092*
C15	0.7021 (6)	0.0612 (12)	0.9073 (4)	0.0648 (16)
H15	0.7073	0.1653	0.8575	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.101 (4)	0.080 (3)	0.066 (3)	−0.025 (3)	0.011 (3)	−0.002 (2)
O2	0.089 (3)	0.069 (3)	0.058 (2)	−0.032 (2)	0.029 (2)	−0.011 (2)
N1	0.062 (3)	0.042 (3)	0.052 (3)	−0.008 (2)	0.023 (2)	−0.001 (2)
N2	0.070 (3)	0.055 (3)	0.043 (3)	−0.013 (3)	0.023 (3)	−0.004 (2)
N3	0.064 (3)	0.058 (3)	0.042 (3)	−0.006 (3)	0.019 (2)	0.003 (2)
N4	0.060 (3)	0.062 (3)	0.051 (3)	−0.002 (2)	0.018 (3)	0.000 (2)
N5	0.066 (3)	0.060 (3)	0.042 (3)	0.000 (3)	0.018 (2)	0.007 (2)
C1	0.064 (4)	0.050 (4)	0.072 (5)	−0.003 (3)	0.016 (4)	0.010 (4)
C2	0.054 (4)	0.043 (3)	0.065 (4)	0.003 (3)	0.021 (3)	0.009 (3)
C3	0.067 (4)	0.079 (5)	0.099 (5)	0.003 (4)	0.043 (4)	0.019 (4)
C4	0.085 (6)	0.074 (5)	0.132 (7)	−0.004 (4)	0.059 (5)	0.024 (5)
C5	0.070 (5)	0.067 (5)	0.154 (8)	−0.007 (4)	0.029 (6)	0.026 (6)
C6	0.079 (5)	0.066 (5)	0.103 (6)	−0.015 (4)	−0.004 (4)	0.027 (4)
C7	0.063 (4)	0.046 (3)	0.047 (3)	0.004 (3)	0.021 (3)	0.002 (3)
C8	0.074 (4)	0.042 (3)	0.041 (3)	−0.012 (3)	0.021 (3)	−0.006 (3)
C9	0.083 (4)	0.058 (4)	0.053 (4)	−0.018 (3)	0.036 (3)	−0.002 (3)
C10	0.066 (4)	0.044 (3)	0.036 (3)	−0.009 (3)	0.012 (3)	−0.004 (3)
C11	0.056 (4)	0.049 (4)	0.044 (3)	−0.002 (3)	0.012 (3)	0.002 (3)
C12	0.073 (4)	0.063 (4)	0.062 (4)	−0.004 (4)	0.027 (3)	−0.002 (4)
C13	0.080 (5)	0.068 (5)	0.078 (4)	0.000 (4)	0.025 (4)	−0.006 (4)
C14	0.073 (5)	0.063 (5)	0.085 (5)	0.014 (4)	0.005 (4)	0.002 (4)
C15	0.088 (5)	0.043 (3)	0.058 (4)	−0.007 (3)	0.009 (4)	0.004 (3)

Geometric parameters (Å, º) top

O1—C1	1.358 (6)	C4—H4	0.930
O1—H1	0.820	C5—C6	1.369 (9)
O2—C8	1.220 (6)	C5—H5	0.930
N1—C7	1.282 (6)	C6—H6	0.930
N1—N2	1.372 (5)	C7—H7	0.930
N2—C8	1.351 (6)	C8—C9	1.502 (7)
N2—H2	0.860	C9—H9A	0.970
N3—N4	1.345 (6)	C9—H9B	0.970
N3—C10	1.354 (6)	C10—C11	1.382 (6)
N3—C9	1.449 (5)	C10—C15	1.387 (7)
N4—N5	1.312 (5)	C11—C12	1.400 (7)
N5—C11	1.375 (6)	C12—C13	1.359 (7)
C1—C2	1.385 (7)	C12—H12	0.930
C1—C6	1.389 (7)	C13—C14	1.389 (8)
C2—C3	1.385 (7)	C13—H13	0.930
C2—C7	1.436 (7)	C14—C15	1.373 (8)
C3—C4	1.369 (8)	C14—H14	0.930
C3—H3	0.930	C15—H15	0.930
C4—C5	1.389 (9)

C1—O1—H1	109.5	N1—C7—H7	118.8
C7—N1—N2	117.1 (4)	C2—C7—H7	118.8
C8—N2—N1	119.5 (4)	O2—C8—N2	121.9 (5)
C8—N2—H2	120.3	O2—C8—C9	123.0 (5)
N1—N2—H2	120.3	N2—C8—C9	115.1 (5)
N4—N3—C10	110.3 (4)	N3—C9—C8	111.7 (4)
N4—N3—C9	119.6 (5)	N3—C9—H9A	109.3
C10—N3—C9	130.0 (5)	C8—C9—H9A	109.3
N5—N4—N3	108.7 (4)	N3—C9—H9B	109.3
N4—N5—C11	107.9 (4)	C8—C9—H9B	109.3
O1—C1—C2	122.8 (5)	H9A—C9—H9B	107.9
O1—C1—C6	116.1 (6)	N3—C10—C11	104.8 (4)
C2—C1—C6	121.1 (6)	N3—C10—C15	133.2 (5)
C1—C2—C3	117.9 (6)	C11—C10—C15	122.0 (5)
C1—C2—C7	122.1 (5)	N5—C11—C10	108.3 (4)
C3—C2—C7	120.0 (6)	N5—C11—C12	130.0 (5)
C4—C3—C2	121.6 (7)	C10—C11—C12	121.7 (5)
C4—C3—H3	119.2	C13—C12—C11	115.6 (5)
C2—C3—H3	119.2	C13—C12—H12	122.2
C3—C4—C5	119.6 (7)	C11—C12—H12	122.2
C3—C4—H4	120.2	C12—C13—C14	122.9 (6)
C5—C4—H4	120.2	C12—C13—H13	118.6
C6—C5—C4	120.0 (7)	C14—C13—H13	118.6
C6—C5—H5	120.0	C15—C14—C13	121.9 (6)
C4—C5—H5	120.0	C15—C14—H14	119.0
C5—C6—C1	119.7 (7)	C13—C14—H14	119.0
C5—C6—H6	120.2	C14—C15—C10	115.9 (5)
C1—C6—H6	120.2	C14—C15—H15	122.1
N1—C7—C2	122.4 (5)	C10—C15—H15	122.1

C7—N1—N2—C8	176.6 (5)	C10—N3—C9—C8	−84.5 (6)
C10—N3—N4—N5	−0.6 (5)	O2—C8—C9—N3	−1.5 (8)
C9—N3—N4—N5	175.2 (4)	N2—C8—C9—N3	−179.9 (5)
N3—N4—N5—C11	−0.5 (6)	N4—N3—C10—C11	1.5 (5)
O1—C1—C2—C3	179.5 (6)	C9—N3—C10—C11	−173.8 (5)
C6—C1—C2—C3	0.3 (8)	N4—N3—C10—C15	−179.4 (5)
O1—C1—C2—C7	−2.6 (8)	C9—N3—C10—C15	5.4 (8)
C6—C1—C2—C7	178.1 (5)	N4—N5—C11—C10	1.4 (6)
C1—C2—C3—C4	0.8 (9)	N4—N5—C11—C12	179.8 (5)
C7—C2—C3—C4	−177.1 (5)	N3—C10—C11—N5	−1.8 (5)
C2—C3—C4—C5	−0.7 (10)	C15—C10—C11—N5	179.0 (5)
C3—C4—C5—C6	−0.4 (10)	N3—C10—C11—C12	179.7 (5)
C4—C5—C6—C1	1.4 (10)	C15—C10—C11—C12	0.4 (7)
O1—C1—C6—C5	179.3 (6)	N5—C11—C12—C13	−178.4 (5)
C2—C1—C6—C5	−1.4 (9)	C10—C11—C12—C13	−0.2 (8)
N2—N1—C7—C2	−179.3 (4)	C11—C12—C13—C14	1.2 (9)
C1—C2—C7—N1	3.8 (8)	C12—C13—C14—C15	−2.5 (10)
C3—C2—C7—N1	−178.3 (5)	C13—C14—C15—C10	2.5 (8)
N1—N2—C8—O2	−178.0 (5)	N3—C10—C15—C14	179.4 (5)
N1—N2—C8—C9	0.4 (7)	C11—C10—C15—C14	−1.5 (7)
N4—N3—C9—C8	100.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N5ⁱ	0.86	2.07	2.927 (5)	172
O1—H1···N1	0.82	1.92	2.638 (6)	145

Symmetry code: (i) x, −y−1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₅O₂
M_r	295.30
Crystal system, space group	Monoclinic, Pc
Temperature (K)	298
a, b, c (Å)	10.644 (3), 4.4834 (12), 15.807 (4)
β (°)	105.672 (6)
V (Å³)	726.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.14 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3578, 1291, 752
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.095, 1.00
No. of reflections	1291
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).