2-(1H-Benzotriazol-1-yl)-N′-(propan-2-yl­idene)acetohydrazide

In the title compound, C₁₁H₁₃N₅O, which was synthesized by the reaction of 2-(1H-benzotriazol-1-yl)acetohydrazide with acetone, all bond lengths and angles are normal. Weak inter­molecular N—H...O hydrogen bonds link the mol­ecules into chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.051
• wR factor = 0.187
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

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Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.51 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C5
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C2
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

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

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

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S1. Comment

In recent years, 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) and biological systems (Anderson et al., 1997). 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, (I), was synthesized and its crystal structure determined.

In (I) (Fig. 1), 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 N—H···O hydrogen bonds (Table 1, Fig. 2).

Related literature

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).

S2. Experimental

The 2-(1H-benzo[d][1,2,3]triazol-1-yl)acetohydrazide (1 mmol, 191.2 mg) was added to acetone solvent (20 ml). The mixture was stirred under reflux conditions (343 K) for 3 h to give a clear solution. The solution was filtered and after a week colourless crystals suitable for X-ray diffraction study were obtained. M.p. 207–208 K. Analysis: calculated for C₁₁H₁₃N₅O: C 57.13, H 5.67, N 30.27%; found: C57.10, H 5.71, N 30.22%.

S3. Refinement

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, with U_iso(H) = 1.2–1.5U_eq of the parent atom.

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (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

	Fig. 1. The molecular structure of (I) showing the atomic numbering and displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A portion of the crystal packing showing the hydrogen-bonded (dashed lines) chain of the molecules. H atoms have been omitted for clarity.

2-(1H-Benzotriazol-1-yl)-N'-(propan-2-ylidene)acetohydrazide

Crystal data

C11H13N5O	F(000) = 488
Mr = 231.26	Dx = 1.297 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1111 reflections
a = 10.841 (2) Å	θ = 2.4–25.7°
b = 13.426 (3) Å	µ = 0.09 mm^−1
c = 8.2811 (17) Å	T = 295 K
β = 100.737 (4)°	Block, colourless
V = 1184.3 (4) Å^3	0.15 × 0.12 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	2094 independent reflections
Radiation source: fine-focus sealed tube	1325 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ϕ and ω scans	θmax = 25.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→7
Tmin = 0.987, Tmax = 0.991	k = −15→15
6155 measured reflections	l = −9→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.187	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.1178P)^2 + 0.0018P] where P = (Fo^2 + 2Fc^2)/3
2094 reflections	(Δ/σ)max = 0.002
156 parameters	Δρmax = 0.18 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.22589 (17)	0.83827 (14)	0.08278 (19)	0.0729 (6)
N1	0.40099 (19)	0.91461 (15)	0.3268 (2)	0.0556 (6)
N2	0.3838 (2)	1.01387 (19)	0.3451 (3)	0.0759 (7)
N3	0.4713 (3)	1.06118 (16)	0.2900 (3)	0.0789 (8)
N4	0.05295 (19)	0.70349 (16)	0.1188 (2)	0.0602 (6)
N5	0.13678 (18)	0.74222 (15)	0.2524 (2)	0.0587 (6)
H5	0.1346	0.7241	0.3514	0.070*
C1	−0.1164 (3)	0.6016 (2)	−0.0022 (4)	0.0843 (10)
H1A	−0.0926	0.6281	−0.0996	0.126*
H1B	−0.2009	0.6213	0.0016	0.126*
H1C	−0.1113	0.5302	−0.0037	0.126*
C2	−0.0295 (2)	0.6409 (2)	0.1464 (3)	0.0591 (7)
C3	−0.0470 (3)	0.6041 (3)	0.3097 (4)	0.0995 (12)
H3A	0.0069	0.5479	0.3410	0.149*
H3B	−0.1328	0.5844	0.3040	0.149*
H3C	−0.0263	0.6561	0.3898	0.149*
C4	0.2205 (2)	0.80851 (19)	0.2198 (3)	0.0550 (7)
C5	0.3128 (3)	0.8439 (2)	0.3710 (3)	0.0744 (9)
H5A	0.2669	0.8747	0.4478	0.089*
H5B	0.3581	0.7872	0.4251	0.089*
C6	0.5010 (2)	0.89849 (16)	0.2542 (3)	0.0471 (6)
C7	0.5460 (2)	0.99256 (18)	0.2310 (3)	0.0577 (7)
C8	0.6471 (4)	1.0065 (3)	0.1553 (4)	0.0903 (11)
H8	0.6770	1.0699	0.1395	0.108*
C9	0.7013 (3)	0.9248 (5)	0.1048 (4)	0.1078 (14)
H9	0.7700	0.9321	0.0533	0.129*
C10	0.6563 (4)	0.8293 (4)	0.1283 (4)	0.1016 (13)
H10	0.6956	0.7747	0.0906	0.122*
C11	0.5558 (3)	0.8132 (2)	0.2054 (3)	0.0691 (8)
H11	0.5269	0.7497	0.2234	0.083*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0772 (13)	0.1055 (15)	0.0345 (10)	−0.0323 (10)	0.0061 (8)	0.0034 (8)
N1	0.0561 (13)	0.0654 (13)	0.0429 (11)	−0.0076 (10)	0.0033 (10)	−0.0075 (9)
N2	0.0823 (18)	0.0720 (16)	0.0655 (15)	0.0156 (13)	−0.0069 (13)	−0.0223 (12)
N3	0.103 (2)	0.0483 (13)	0.0728 (17)	0.0026 (14)	−0.0159 (15)	−0.0053 (11)
N4	0.0559 (13)	0.0835 (14)	0.0378 (11)	−0.0124 (11)	0.0004 (9)	−0.0005 (9)
N5	0.0576 (13)	0.0859 (15)	0.0309 (10)	−0.0169 (11)	0.0034 (9)	0.0024 (9)
C1	0.0673 (19)	0.112 (2)	0.070 (2)	−0.0265 (16)	0.0024 (15)	−0.0121 (15)
C2	0.0534 (16)	0.0739 (17)	0.0499 (15)	−0.0065 (13)	0.0091 (12)	−0.0015 (12)
C3	0.104 (3)	0.132 (3)	0.063 (2)	−0.053 (2)	0.0172 (18)	0.0070 (17)
C4	0.0533 (15)	0.0777 (16)	0.0343 (13)	−0.0093 (13)	0.0085 (11)	−0.0025 (11)
C5	0.0662 (18)	0.114 (2)	0.0405 (14)	−0.0309 (16)	0.0047 (12)	−0.0013 (14)
C6	0.0518 (14)	0.0485 (14)	0.0371 (12)	−0.0028 (11)	−0.0020 (10)	−0.0015 (9)
C7	0.0669 (17)	0.0536 (15)	0.0470 (14)	−0.0098 (13)	−0.0037 (12)	0.0057 (11)
C8	0.088 (2)	0.118 (3)	0.0598 (19)	−0.042 (2)	−0.0013 (17)	0.0257 (18)
C9	0.069 (2)	0.197 (5)	0.057 (2)	−0.012 (3)	0.0109 (17)	0.002 (3)
C10	0.085 (3)	0.145 (4)	0.068 (2)	0.046 (2)	−0.0028 (19)	−0.034 (2)
C11	0.081 (2)	0.0591 (16)	0.0598 (17)	0.0144 (14)	−0.0050 (15)	−0.0113 (12)

Geometric parameters (Å, º)

O1—C4	1.215 (3)	C3—H3B	0.9600
N1—C6	1.352 (3)	C3—H3C	0.9600
N1—N2	1.358 (3)	C4—C5	1.526 (3)
N1—C5	1.441 (3)	C5—H5A	0.9700
N2—N3	1.293 (3)	C5—H5B	0.9700
N3—C7	1.375 (4)	C6—C7	1.380 (3)
N4—C2	1.278 (3)	C6—C11	1.384 (3)
N4—N5	1.395 (3)	C7—C8	1.373 (4)
N5—C4	1.334 (3)	C8—C9	1.347 (5)
N5—H5	0.8600	C8—H8	0.9300
C1—C2	1.500 (4)	C9—C10	1.399 (6)
C1—H1A	0.9600	C9—H9	0.9300
C1—H1B	0.9600	C10—C11	1.379 (5)
C1—H1C	0.9600	C10—H10	0.9300
C2—C3	1.485 (4)	C11—H11	0.9300
C3—H3A	0.9600
C6—N1—N2	110.2 (2)	N5—C4—C5	114.2 (2)
C6—N1—C5	129.2 (2)	N1—C5—C4	111.2 (2)
N2—N1—C5	120.4 (2)	N1—C5—H5A	109.4
N3—N2—N1	108.5 (2)	C4—C5—H5A	109.4
N2—N3—C7	108.4 (2)	N1—C5—H5B	109.4
C2—N4—N5	118.48 (19)	C4—C5—H5B	109.4
C4—N5—N4	117.10 (18)	H5A—C5—H5B	108.0
C4—N5—H5	121.4	N1—C6—C7	104.4 (2)
N4—N5—H5	121.4	N1—C6—C11	133.3 (2)
C2—C1—H1A	109.5	C7—C6—C11	122.3 (3)
C2—C1—H1B	109.5	C8—C7—N3	130.1 (3)
H1A—C1—H1B	109.5	C8—C7—C6	121.4 (3)
C2—C1—H1C	109.5	N3—C7—C6	108.5 (2)
H1A—C1—H1C	109.5	C9—C8—C7	117.6 (3)
H1B—C1—H1C	109.5	C9—C8—H8	121.2
N4—C2—C3	126.5 (2)	C7—C8—H8	121.2
N4—C2—C1	116.0 (2)	C8—C9—C10	121.3 (3)
C3—C2—C1	117.6 (2)	C8—C9—H9	119.4
C2—C3—H3A	109.5	C10—C9—H9	119.4
C2—C3—H3B	109.5	C11—C10—C9	122.3 (3)
H3A—C3—H3B	109.5	C11—C10—H10	118.9
C2—C3—H3C	109.5	C9—C10—H10	118.9
H3A—C3—H3C	109.5	C10—C11—C6	115.1 (3)
H3B—C3—H3C	109.5	C10—C11—H11	122.4
O1—C4—N5	124.1 (2)	C6—C11—H11	122.4
O1—C4—C5	121.7 (2)
C6—N1—N2—N3	−1.5 (3)	C5—N1—C6—C11	−3.4 (4)
C5—N1—N2—N3	−177.0 (2)	N2—N3—C7—C8	177.2 (3)
N1—N2—N3—C7	1.3 (3)	N2—N3—C7—C6	−0.7 (3)
C2—N4—N5—C4	−179.0 (2)	N1—C6—C7—C8	−178.3 (2)
N5—N4—C2—C3	0.3 (4)	C11—C6—C7—C8	1.1 (4)
N5—N4—C2—C1	−179.7 (2)	N1—C6—C7—N3	−0.2 (2)
N4—N5—C4—O1	1.7 (4)	C11—C6—C7—N3	179.2 (2)
N4—N5—C4—C5	−177.3 (2)	N3—C7—C8—C9	−178.0 (3)
C6—N1—C5—C4	−75.1 (3)	C6—C7—C8—C9	−0.2 (4)
N2—N1—C5—C4	99.4 (3)	C7—C8—C9—C10	0.1 (5)
O1—C4—C5—N1	0.5 (4)	C8—C9—C10—C11	−0.8 (5)
N5—C4—C5—N1	179.5 (2)	C9—C10—C11—C6	1.5 (4)
N2—N1—C6—C7	1.0 (2)	N1—C6—C11—C10	177.6 (2)
C5—N1—C6—C7	176.0 (2)	C7—C6—C11—C10	−1.6 (3)
N2—N1—C6—C11	−178.4 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···O1^i	0.86	2.16	2.933 (2)	150

Symmetry code: (i) x, −y+3/2, z+1/2.