organic compounds
The title compound, C5H9ON3, was synthesized by the reaction of 2-hydrazinylethanol with 3-methoxypropanenitrile. The pyrazole ring system is essentially planar. Molecules are linked by O—HN and N—HO hydrogen bonds.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042061/bh2051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042061/bh2051Isup2.hkl |
CCDC reference: 627316
Computing details top
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
5-Amino-1-(2-hydroxyethyl)pyrazole top
Crystal data top
C5H9N3O | F(000) = 272 |
Mr = 127.15 | Dx = 1.363 Mg m−3 |
Monoclinic, P21/n | Melting point = 379–381 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.977 (2) Å | Cell parameters from 1169 reflections |
b = 5.5467 (14) Å | θ = 4.0–24.7° |
c = 12.562 (3) Å | µ = 0.10 mm−1 |
β = 97.774 (4)° | T = 294 K |
V = 619.7 (3) Å3 | Rod, colourless |
Z = 4 | 0.22 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART 1000 diffractometer | 1094 independent reflections |
Radiation source: fine-focus sealed tube | 853 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
φ and ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −9→10 |
Tmin = 0.978, Tmax = 0.988 | k = −6→6 |
3003 measured reflections | l = −14→8 |
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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0417P)2 + 0.0839P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
1094 reflections | Δρmax = 0.15 e Å−3 |
94 parameters | Δρmin = −0.17 e Å−3 |
3 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.045 (6) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.17221 (12) | 0.1734 (2) | 0.58285 (9) | 0.0529 (4) | |
H1 | 0.2487 (19) | 0.096 (4) | 0.5984 (15) | 0.079* | |
N1 | 0.00693 (13) | 0.3657 (2) | 0.74470 (9) | 0.0350 (4) | |
N2 | 0.05615 (14) | 0.4198 (2) | 0.85014 (9) | 0.0394 (4) | |
N3 | −0.15422 (17) | 0.0992 (3) | 0.63531 (12) | 0.0461 (4) | |
C1 | 0.19681 (17) | 0.4116 (3) | 0.62165 (12) | 0.0448 (5) | |
H1A | 0.2253 | 0.5138 | 0.5651 | 0.054* | |
H1B | 0.2781 | 0.4129 | 0.6810 | 0.054* | |
C2 | 0.05562 (17) | 0.5066 (3) | 0.65862 (11) | 0.0398 (4) | |
H2A | 0.0726 | 0.6716 | 0.6829 | 0.048* | |
H2B | −0.0240 | 0.5084 | 0.5982 | 0.048* | |
C3 | −0.08801 (15) | 0.1754 (3) | 0.73550 (12) | 0.0345 (4) | |
C4 | −0.10492 (17) | 0.1050 (3) | 0.83809 (12) | 0.0406 (4) | |
H4 | −0.1642 | −0.0199 | 0.8584 | 0.049* | |
C5 | −0.01432 (17) | 0.2606 (3) | 0.90483 (12) | 0.0410 (4) | |
H5 | −0.0040 | 0.2544 | 0.9794 | 0.049* | |
H3A | −0.0928 (18) | 0.083 (3) | 0.5894 (13) | 0.057 (6)* | |
H3B | −0.2097 (19) | −0.030 (3) | 0.6385 (14) | 0.062 (6)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0387 (7) | 0.0626 (9) | 0.0566 (8) | 0.0053 (6) | 0.0035 (6) | −0.0139 (6) |
N1 | 0.0380 (7) | 0.0355 (7) | 0.0310 (7) | 0.0002 (6) | 0.0024 (5) | −0.0010 (5) |
N2 | 0.0440 (8) | 0.0398 (8) | 0.0329 (7) | −0.0002 (6) | −0.0001 (6) | −0.0024 (6) |
N3 | 0.0441 (9) | 0.0466 (9) | 0.0464 (9) | −0.0046 (7) | 0.0020 (7) | −0.0106 (7) |
C1 | 0.0383 (9) | 0.0542 (11) | 0.0411 (9) | −0.0081 (8) | 0.0022 (7) | 0.0044 (8) |
C2 | 0.0456 (10) | 0.0369 (9) | 0.0357 (9) | −0.0006 (7) | 0.0004 (7) | 0.0046 (7) |
C3 | 0.0295 (8) | 0.0329 (8) | 0.0405 (9) | 0.0027 (6) | 0.0028 (6) | −0.0046 (6) |
C4 | 0.0364 (9) | 0.0390 (9) | 0.0475 (10) | −0.0018 (7) | 0.0097 (7) | 0.0041 (7) |
C5 | 0.0436 (9) | 0.0455 (10) | 0.0344 (8) | 0.0057 (8) | 0.0069 (7) | 0.0024 (7) |
Geometric parameters (Å, º) top
O1—C1 | 1.415 (2) | C1—C2 | 1.503 (2) |
O1—H1 | 0.810 (15) | C1—H1A | 0.9700 |
N1—C3 | 1.3516 (19) | C1—H1B | 0.9700 |
N1—N2 | 1.3717 (16) | C2—H2A | 0.9700 |
N1—C2 | 1.4490 (18) | C2—H2B | 0.9700 |
N2—C5 | 1.330 (2) | C3—C4 | 1.375 (2) |
N3—C3 | 1.3834 (19) | C4—C5 | 1.388 (2) |
N3—H3A | 0.855 (14) | C4—H4 | 0.9300 |
N3—H3B | 0.877 (14) | C5—H5 | 0.9300 |
C1—O1—H1 | 108.7 (15) | N1—C2—H2A | 108.9 |
C3—N1—N2 | 111.74 (12) | C1—C2—H2A | 108.9 |
C3—N1—C2 | 127.44 (12) | N1—C2—H2B | 108.9 |
N2—N1—C2 | 120.82 (12) | C1—C2—H2B | 108.9 |
C5—N2—N1 | 103.89 (12) | H2A—C2—H2B | 107.8 |
C3—N3—H3A | 114.1 (12) | N1—C3—C4 | 106.87 (13) |
C3—N3—H3B | 112.6 (12) | N1—C3—N3 | 120.32 (14) |
H3A—N3—H3B | 111.5 (17) | C4—C3—N3 | 132.67 (15) |
O1—C1—C2 | 109.57 (13) | C3—C4—C5 | 105.04 (13) |
O1—C1—H1A | 109.8 | C3—C4—H4 | 127.5 |
C2—C1—H1A | 109.8 | C5—C4—H4 | 127.5 |
O1—C1—H1B | 109.8 | N2—C5—C4 | 112.44 (14) |
C2—C1—H1B | 109.8 | N2—C5—H5 | 123.8 |
H1A—C1—H1B | 108.2 | C4—C5—H5 | 123.8 |
N1—C2—C1 | 113.16 (13) | ||
C3—N1—N2—C5 | −1.41 (15) | N2—N1—C3—N3 | 177.53 (13) |
C2—N1—N2—C5 | 178.07 (13) | C2—N1—C3—N3 | −1.9 (2) |
C3—N1—C2—C1 | −90.70 (18) | N1—C3—C4—C5 | −0.82 (17) |
N2—N1—C2—C1 | 89.90 (16) | N3—C3—C4—C5 | −176.24 (16) |
O1—C1—C2—N1 | 60.44 (17) | N1—N2—C5—C4 | 0.86 (16) |
N2—N1—C3—C4 | 1.43 (16) | C3—C4—C5—N2 | −0.04 (18) |
C2—N1—C3—C4 | −178.01 (13) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2i | 0.81 (2) | 2.04 (2) | 2.8422 (18) | 175 (2) |
N3—H3A···O1ii | 0.86 (1) | 2.61 (2) | 3.1149 (19) | 119 (1) |
N3—H3A···O1 | 0.86 (1) | 2.44 (2) | 3.117 (2) | 136 (2) |
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2; (ii) −x, −y, −z+1. |