Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704158X/cv2290sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704158X/cv2290Isup2.hkl |
CCDC reference: 657951
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.106
- Data-to-parameter ratio = 12.0
checkCIF/PLATON results
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In the complex [Cu(L)2] (HL=4-salicylideneamino-3,5-dimethanol-1,2,4-triazole) (Yi et al., 2004), all bond lengths and angles in L are comparable with those found in the title compound.
A mixture of lactic acid (1 mmol) and hydrazine hydrate (1.05 mmol) was well stirred at room temperature for 10 minutes. The crude compound was purified by silica gel column chromatography. Elemental analysis: calculated for C4H8N4O2: C 33.33, H 5.59, N 38.87%; found: C 33.38, H 5.52, N 38.75%.
The methylene H atoms were placed in idealized positions and constrained to ride on their parent atoms with methylene C—H distances of 0.97 Å. The Uiso(H) values were set at 1.2Ueq(C). The hydroxy H atoms were placed in idealized positions and constrained to ride on their parent atoms with O—H distances of 0.82 Å. The Uiso(H) values were set at 1.5 Ueq(O). The amino H atoms were placed in idealized positions and constrained to ride on their parent atoms with N—H distances of 0.90 Å. The Uiso(H) values were set at 1.2 Ueq(N).
In this paper, we present the title compound, 4-amino-3,5-bis(1-hydroxyethyl)-l,2,4-triazole, (I), synthesized through the condensation of lactic acid and hydrazine hydrate under solvent-free conditions.
In (I) (Fig. 1), all bond lengths and angles are normal and comparable to those observed in the complex [Cu(L)2] (HL=4-salicylideneamino-3,5-dimethanol-1,2,4-triazole) (Yi et al., 2004)
In the crystal, there exist typical intermolecular N—H···O and O—H···N hydrogen bonds (Table 1), which assemble the molecules into infinite two-dimensional sheets (Fig. 2).
In the complex [Cu(L)2] (HL=4-salicylideneamino-3,5-dimethanol-1,2,4-triazole) (Yi et al., 2004), all bond lengths and angles in L are comparable with those found in the title compound.
Data collection: SMART (Siemens, 1996); cell refinement: SMART; 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.
C4H8N4O2 | Dx = 1.530 Mg m−3 |
Mr = 144.14 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 2134 reflections |
a = 8.7936 (17) Å | θ = 2.5–27.6° |
b = 8.8609 (18) Å | µ = 0.12 mm−1 |
c = 16.058 (2) Å | T = 298 K |
V = 1251.3 (4) Å3 | Block, colourless |
Z = 8 | 0.54 × 0.47 × 0.40 mm |
F(000) = 608 |
Bruker SMART CCD area-detector diffractometer | 1107 independent reflections |
Radiation source: fine-focus sealed tube | 853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.048 |
φ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −5→10 |
Tmin = 0.936, Tmax = 0.952 | k = −10→9 |
4961 measured reflections | l = −19→17 |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.106 | w = 1/[σ2(Fo2) + (0.045P)2 + 0.8519P] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max < 0.001 |
1107 reflections | Δρmax = 0.21 e Å−3 |
92 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997a), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.061 (4) |
C4H8N4O2 | V = 1251.3 (4) Å3 |
Mr = 144.14 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 8.7936 (17) Å | µ = 0.12 mm−1 |
b = 8.8609 (18) Å | T = 298 K |
c = 16.058 (2) Å | 0.54 × 0.47 × 0.40 mm |
Bruker SMART CCD area-detector diffractometer | 1107 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 853 reflections with I > 2σ(I) |
Tmin = 0.936, Tmax = 0.952 | Rint = 0.048 |
4961 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.106 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.21 e Å−3 |
1107 reflections | Δρmin = −0.20 e Å−3 |
92 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
N1 | −0.06178 (18) | 0.76742 (18) | 0.23561 (10) | 0.0344 (4) | |
N2 | 0.05790 (18) | 0.66499 (18) | 0.23983 (10) | 0.0349 (4) | |
N3 | 0.01255 (17) | 0.71644 (17) | 0.10961 (9) | 0.0307 (4) | |
N4 | 0.0336 (2) | 0.7147 (2) | 0.02318 (10) | 0.0443 (5) | |
H4A | 0.0599 | 0.8063 | 0.0037 | 0.053* | |
H4B | −0.0503 | 0.6824 | −0.0034 | 0.053* | |
O1 | 0.16445 (16) | 0.38730 (15) | 0.11444 (8) | 0.0402 (4) | |
H1 | 0.1196 | 0.3501 | 0.1542 | 0.060* | |
O2 | −0.13453 (18) | 1.04642 (15) | 0.10268 (8) | 0.0444 (5) | |
H2 | −0.0956 | 1.0836 | 0.1443 | 0.067* | |
C1 | 0.1008 (2) | 0.6365 (2) | 0.16332 (11) | 0.0307 (5) | |
C2 | −0.0871 (2) | 0.7968 (2) | 0.15687 (11) | 0.0304 (5) | |
C3 | 0.2228 (2) | 0.5305 (2) | 0.13717 (13) | 0.0385 (5) | |
H3A | 0.2771 | 0.5733 | 0.0902 | 0.046* | |
H3B | 0.2945 | 0.5182 | 0.1825 | 0.046* | |
C4 | −0.2009 (2) | 0.9057 (2) | 0.12349 (12) | 0.0378 (5) | |
H4C | −0.2482 | 0.8629 | 0.0743 | 0.045* | |
H4D | −0.2798 | 0.9215 | 0.1648 | 0.045* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0390 (9) | 0.0334 (9) | 0.0310 (9) | 0.0043 (7) | 0.0023 (7) | 0.0010 (7) |
N2 | 0.0402 (10) | 0.0332 (9) | 0.0313 (9) | 0.0032 (8) | 0.0007 (7) | 0.0027 (7) |
N3 | 0.0347 (9) | 0.0327 (9) | 0.0246 (8) | −0.0026 (7) | 0.0005 (6) | −0.0009 (7) |
N4 | 0.0573 (12) | 0.0504 (11) | 0.0253 (9) | 0.0000 (9) | 0.0020 (8) | 0.0000 (8) |
O1 | 0.0542 (9) | 0.0333 (8) | 0.0331 (8) | 0.0002 (7) | 0.0046 (6) | −0.0030 (6) |
O2 | 0.0614 (10) | 0.0369 (9) | 0.0350 (8) | −0.0017 (7) | −0.0072 (7) | 0.0048 (6) |
C1 | 0.0315 (10) | 0.0287 (10) | 0.0320 (10) | −0.0039 (8) | 0.0007 (8) | 0.0008 (8) |
C2 | 0.0321 (10) | 0.0280 (10) | 0.0312 (10) | −0.0036 (8) | −0.0008 (8) | −0.0010 (8) |
C3 | 0.0365 (11) | 0.0379 (11) | 0.0411 (11) | 0.0003 (9) | 0.0044 (9) | 0.0007 (9) |
C4 | 0.0378 (11) | 0.0387 (11) | 0.0369 (11) | 0.0020 (9) | −0.0051 (9) | 0.0007 (9) |
N1—C2 | 1.310 (2) | O1—H1 | 0.8200 |
N1—N2 | 1.391 (2) | O2—C4 | 1.417 (2) |
N2—C1 | 1.310 (2) | O2—H2 | 0.8200 |
N3—C1 | 1.359 (2) | C1—C3 | 1.486 (3) |
N3—C2 | 1.361 (2) | C2—C4 | 1.489 (3) |
N3—N4 | 1.400 (2) | C3—H3A | 0.9700 |
N4—H4A | 0.9000 | C3—H3B | 0.9700 |
N4—H4B | 0.9000 | C4—H4C | 0.9700 |
O1—C3 | 1.417 (2) | C4—H4D | 0.9700 |
C2—N1—N2 | 107.79 (14) | N1—C2—C4 | 126.18 (17) |
C1—N2—N1 | 107.30 (15) | N3—C2—C4 | 124.81 (17) |
C1—N3—C2 | 106.64 (15) | O1—C3—C1 | 112.19 (16) |
C1—N3—N4 | 123.21 (16) | O1—C3—H3A | 109.2 |
C2—N3—N4 | 130.08 (16) | C1—C3—H3A | 109.2 |
N3—N4—H4A | 111.6 | O1—C3—H3B | 109.2 |
N3—N4—H4B | 111.4 | C1—C3—H3B | 109.2 |
H4A—N4—H4B | 109.5 | H3A—C3—H3B | 107.9 |
C3—O1—H1 | 109.5 | O2—C4—C2 | 112.22 (16) |
C4—O2—H2 | 109.5 | O2—C4—H4C | 109.2 |
N2—C1—N3 | 109.32 (16) | C2—C4—H4C | 109.2 |
N2—C1—C3 | 126.46 (17) | O2—C4—H4D | 109.2 |
N3—C1—C3 | 124.19 (17) | C2—C4—H4D | 109.2 |
N1—C2—N3 | 108.94 (16) | H4C—C4—H4D | 107.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2i | 0.82 | 2.02 | 2.820 (2) | 164 |
N4—H4B···O1ii | 0.90 | 2.14 | 2.955 (2) | 151 |
N4—H4A···O2iii | 0.90 | 2.25 | 3.058 (2) | 150 |
O1—H1···N1iv | 0.82 | 1.98 | 2.782 (2) | 165 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C4H8N4O2 |
Mr | 144.14 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 298 |
a, b, c (Å) | 8.7936 (17), 8.8609 (18), 16.058 (2) |
V (Å3) | 1251.3 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.54 × 0.47 × 0.40 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.936, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4961, 1107, 853 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.106, 1.00 |
No. of reflections | 1107 |
No. of parameters | 92 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.20 |
Computer programs: SMART (Siemens, 1996), SMART, SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N2i | 0.82 | 2.02 | 2.820 (2) | 164.0 |
N4—H4B···O1ii | 0.90 | 2.14 | 2.955 (2) | 150.9 |
N4—H4A···O2iii | 0.90 | 2.25 | 3.058 (2) | 149.6 |
O1—H1···N1iv | 0.82 | 1.98 | 2.782 (2) | 165.4 |
Symmetry codes: (i) −x, y+1/2, −z+1/2; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z; (iv) −x, y−1/2, −z+1/2. |
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In this paper, we present the title compound, 4-amino-3,5-bis(1-hydroxyethyl)-l,2,4-triazole, (I), synthesized through the condensation of lactic acid and hydrazine hydrate under solvent-free conditions.
In (I) (Fig. 1), all bond lengths and angles are normal and comparable to those observed in the complex [Cu(L)2] (HL=4-salicylideneamino-3,5-dimethanol-1,2,4-triazole) (Yi et al., 2004)
In the crystal, there exist typical intermolecular N—H···O and O—H···N hydrogen bonds (Table 1), which assemble the molecules into infinite two-dimensional sheets (Fig. 2).