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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—H...N and N—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042061/bh2051sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042061/bh2051Isup2.hkl
Contains datablock I

CCDC reference: 627316

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.032
  • wR factor = 0.087
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT150_ALERT_1_C Volume as Calculated Differs from that Given ... 619.70 Ang-3 PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3B ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H3A .. O1 .. 2.61 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

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
C5H9N3OF(000) = 272
Mr = 127.15Dx = 1.363 Mg m3
Monoclinic, P21/nMelting point = 379–381 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71073 Å
a = 8.977 (2) ÅCell parameters from 1169 reflections
b = 5.5467 (14) Åθ = 4.0–24.7°
c = 12.562 (3) ŵ = 0.10 mm1
β = 97.774 (4)°T = 294 K
V = 619.7 (3) Å3Rod, colourless
Z = 40.22 × 0.20 × 0.12 mm
Data collection top
Bruker SMART 1000
diffractometer
1094 independent reflections
Radiation source: fine-focus sealed tube853 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
φ and ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 910
Tmin = 0.978, Tmax = 0.988k = 66
3003 measured reflectionsl = 148
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)] = 0.032H 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 reflectionsΔρmax = 0.15 e Å3
94 parametersΔρmin = 0.17 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.045 (6)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.17221 (12)0.1734 (2)0.58285 (9)0.0529 (4)
H10.2487 (19)0.096 (4)0.5984 (15)0.079*
N10.00693 (13)0.3657 (2)0.74470 (9)0.0350 (4)
N20.05615 (14)0.4198 (2)0.85014 (9)0.0394 (4)
N30.15422 (17)0.0992 (3)0.63531 (12)0.0461 (4)
C10.19681 (17)0.4116 (3)0.62165 (12)0.0448 (5)
H1A0.22530.51380.56510.054*
H1B0.27810.41290.68100.054*
C20.05562 (17)0.5066 (3)0.65862 (11)0.0398 (4)
H2A0.07260.67160.68290.048*
H2B0.02400.50840.59820.048*
C30.08801 (15)0.1754 (3)0.73550 (12)0.0345 (4)
C40.10492 (17)0.1050 (3)0.83809 (12)0.0406 (4)
H40.16420.01990.85840.049*
C50.01432 (17)0.2606 (3)0.90483 (12)0.0410 (4)
H50.00400.25440.97940.049*
H3A0.0928 (18)0.083 (3)0.5894 (13)0.057 (6)*
H3B0.2097 (19)0.030 (3)0.6385 (14)0.062 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0387 (7)0.0626 (9)0.0566 (8)0.0053 (6)0.0035 (6)0.0139 (6)
N10.0380 (7)0.0355 (7)0.0310 (7)0.0002 (6)0.0024 (5)0.0010 (5)
N20.0440 (8)0.0398 (8)0.0329 (7)0.0002 (6)0.0001 (6)0.0024 (6)
N30.0441 (9)0.0466 (9)0.0464 (9)0.0046 (7)0.0020 (7)0.0106 (7)
C10.0383 (9)0.0542 (11)0.0411 (9)0.0081 (8)0.0022 (7)0.0044 (8)
C20.0456 (10)0.0369 (9)0.0357 (9)0.0006 (7)0.0004 (7)0.0046 (7)
C30.0295 (8)0.0329 (8)0.0405 (9)0.0027 (6)0.0028 (6)0.0046 (6)
C40.0364 (9)0.0390 (9)0.0475 (10)0.0018 (7)0.0097 (7)0.0041 (7)
C50.0436 (9)0.0455 (10)0.0344 (8)0.0057 (8)0.0069 (7)0.0024 (7)
Geometric parameters (Å, º) top
O1—C11.415 (2)C1—C21.503 (2)
O1—H10.810 (15)C1—H1A0.9700
N1—C31.3516 (19)C1—H1B0.9700
N1—N21.3717 (16)C2—H2A0.9700
N1—C21.4490 (18)C2—H2B0.9700
N2—C51.330 (2)C3—C41.375 (2)
N3—C31.3834 (19)C4—C51.388 (2)
N3—H3A0.855 (14)C4—H40.9300
N3—H3B0.877 (14)C5—H50.9300
C1—O1—H1108.7 (15)N1—C2—H2A108.9
C3—N1—N2111.74 (12)C1—C2—H2A108.9
C3—N1—C2127.44 (12)N1—C2—H2B108.9
N2—N1—C2120.82 (12)C1—C2—H2B108.9
C5—N2—N1103.89 (12)H2A—C2—H2B107.8
C3—N3—H3A114.1 (12)N1—C3—C4106.87 (13)
C3—N3—H3B112.6 (12)N1—C3—N3120.32 (14)
H3A—N3—H3B111.5 (17)C4—C3—N3132.67 (15)
O1—C1—C2109.57 (13)C3—C4—C5105.04 (13)
O1—C1—H1A109.8C3—C4—H4127.5
C2—C1—H1A109.8C5—C4—H4127.5
O1—C1—H1B109.8N2—C5—C4112.44 (14)
C2—C1—H1B109.8N2—C5—H5123.8
H1A—C1—H1B108.2C4—C5—H5123.8
N1—C2—C1113.16 (13)
C3—N1—N2—C51.41 (15)N2—N1—C3—N3177.53 (13)
C2—N1—N2—C5178.07 (13)C2—N1—C3—N31.9 (2)
C3—N1—C2—C190.70 (18)N1—C3—C4—C50.82 (17)
N2—N1—C2—C189.90 (16)N3—C3—C4—C5176.24 (16)
O1—C1—C2—N160.44 (17)N1—N2—C5—C40.86 (16)
N2—N1—C3—C41.43 (16)C3—C4—C5—N20.04 (18)
C2—N1—C3—C4178.01 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.81 (2)2.04 (2)2.8422 (18)175 (2)
N3—H3A···O1ii0.86 (1)2.61 (2)3.1149 (19)119 (1)
N3—H3A···O10.86 (1)2.44 (2)3.117 (2)136 (2)
Symmetry codes: (i) x+1/2, y1/2, z+3/2; (ii) x, y, z+1.
 

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