In the title molecule, C
9H
9N
3·H
2O, the dihedral angle between the planes of the pyridine and pyrazole rings is 27.52 (2)°. In the crystal structure, intermolecular N—H
O, O—H
N and weak C—H
O hydrogen bonds help stabilize the crystal structure.
Supporting information
CCDC reference: 647272
Key indicators
- Single-crystal X-ray study
- T = 173 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.133
- Data-to-parameter ratio = 14.4
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT093_ALERT_1_A No su's on H-atoms, but refinement reported as . mixed
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C9 H11 N3 O1
Atom count from _chemical_formula_moiety:C9 H29 N3
1 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
2 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
4 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
0 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
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
4-(5-Methyl-1
H-pyrazol-3-yl)pyridine monohydrate
top
Crystal data top
C9H9N3·H20 | F(000) = 376 |
Mr = 177.21 | Dx = 1.233 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 622 reflections |
a = 7.568 (2) Å | θ = 2.7–20.3° |
b = 8.621 (3) Å | µ = 0.08 mm−1 |
c = 14.704 (4) Å | T = 173 K |
β = 95.652 (5)° | Block, colourless |
V = 954.6 (5) Å3 | 0.28 × 0.14 × 0.12 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 1756 independent reflections |
Radiation source: fine-focus sealed tube | 1174 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
φ and ω scans | θmax = 25.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→9 |
Tmin = 0.977, Tmax = 0.990 | k = −10→7 |
4391 measured reflections | l = −13→17 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0596P)2] where P = (Fo2 + 2Fc2)/3 |
1756 reflections | (Δ/σ)max < 0.001 |
122 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
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 | Uiso*/Ueq | |
C1 | 0.7802 (3) | 0.0233 (3) | 0.05441 (17) | 0.0520 (7) | |
H1A | 0.8274 | 0.0951 | 0.0112 | 0.078* | |
H1B | 0.7392 | −0.0717 | 0.0223 | 0.078* | |
H1C | 0.8737 | −0.0025 | 0.1030 | 0.078* | |
C2 | 0.6289 (3) | 0.0975 (2) | 0.09508 (15) | 0.0386 (6) | |
C3 | 0.5312 (3) | 0.0546 (3) | 0.16453 (15) | 0.0415 (6) | |
H3 | 0.5474 | −0.0353 | 0.2018 | 0.050* | |
C4 | 0.4028 (3) | 0.1700 (2) | 0.16944 (15) | 0.0335 (5) | |
C5 | 0.2587 (3) | 0.1782 (2) | 0.22909 (14) | 0.0343 (5) | |
C6 | 0.2735 (3) | 0.1066 (3) | 0.31406 (15) | 0.0435 (6) | |
H6 | 0.3805 | 0.0557 | 0.3361 | 0.052* | |
C7 | 0.1321 (4) | 0.1100 (3) | 0.36604 (16) | 0.0491 (7) | |
H7 | 0.1451 | 0.0595 | 0.4237 | 0.059* | |
C8 | −0.0344 (3) | 0.2515 (3) | 0.25973 (17) | 0.0478 (7) | |
H8 | −0.1421 | 0.3033 | 0.2399 | 0.057* | |
C9 | 0.1012 (3) | 0.2543 (2) | 0.20323 (16) | 0.0423 (6) | |
H9 | 0.0860 | 0.3084 | 0.1467 | 0.051* | |
N1 | −0.0224 (3) | 0.1800 (2) | 0.34037 (14) | 0.0475 (6) | |
N2 | 0.4206 (2) | 0.2798 (2) | 0.10733 (12) | 0.0373 (5) | |
N3 | 0.5592 (2) | 0.23265 (19) | 0.06289 (12) | 0.0381 (5) | |
O1 | 0.7031 (2) | 0.08404 (19) | 0.43854 (11) | 0.0509 (5) | |
H1 | 0.7898 | 0.1192 | 0.4018 | 0.073 (9)* | |
H2 | 0.6774 | −0.0160 | 0.4224 | 0.093 (11)* | |
H3A | 0.6069 | 0.2987 | 0.0198 | 0.054 (7)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0472 (16) | 0.0498 (15) | 0.0602 (16) | 0.0125 (12) | 0.0116 (13) | −0.0040 (13) |
C2 | 0.0409 (14) | 0.0338 (13) | 0.0416 (14) | 0.0039 (10) | 0.0062 (11) | −0.0013 (10) |
C3 | 0.0445 (15) | 0.0341 (13) | 0.0467 (14) | 0.0040 (10) | 0.0081 (12) | 0.0101 (11) |
C4 | 0.0356 (13) | 0.0282 (11) | 0.0371 (13) | −0.0052 (9) | 0.0061 (10) | 0.0003 (10) |
C5 | 0.0391 (14) | 0.0265 (11) | 0.0382 (13) | −0.0067 (9) | 0.0088 (11) | −0.0023 (10) |
C6 | 0.0428 (15) | 0.0451 (14) | 0.0431 (14) | −0.0035 (11) | 0.0068 (11) | 0.0086 (11) |
C7 | 0.0597 (18) | 0.0519 (16) | 0.0368 (14) | −0.0110 (13) | 0.0102 (13) | 0.0057 (12) |
C8 | 0.0427 (16) | 0.0478 (15) | 0.0549 (16) | −0.0006 (11) | 0.0143 (12) | 0.0037 (12) |
C9 | 0.0439 (15) | 0.0418 (14) | 0.0426 (14) | −0.0003 (11) | 0.0108 (11) | 0.0057 (11) |
N1 | 0.0480 (14) | 0.0473 (12) | 0.0497 (13) | −0.0117 (10) | 0.0181 (11) | −0.0035 (10) |
N2 | 0.0428 (12) | 0.0312 (10) | 0.0407 (11) | 0.0026 (8) | 0.0177 (9) | 0.0022 (8) |
N3 | 0.0429 (12) | 0.0320 (10) | 0.0421 (11) | 0.0014 (8) | 0.0171 (9) | 0.0020 (9) |
O1 | 0.0598 (12) | 0.0412 (10) | 0.0572 (11) | −0.0127 (8) | 0.0333 (9) | −0.0125 (8) |
Geometric parameters (Å, º) top
C1—C2 | 1.488 (3) | C6—C7 | 1.375 (3) |
C1—H1A | 0.9800 | C6—H6 | 0.9500 |
C1—H1B | 0.9800 | C7—N1 | 1.337 (3) |
C1—H1C | 0.9800 | C7—H7 | 0.9500 |
C2—N3 | 1.346 (3) | C8—N1 | 1.331 (3) |
C2—C3 | 1.369 (3) | C8—C9 | 1.383 (3) |
C3—C4 | 1.397 (3) | C8—H8 | 0.9500 |
C3—H3 | 0.9500 | C9—H9 | 0.9500 |
C4—N2 | 1.331 (3) | N2—N3 | 1.352 (2) |
C4—C5 | 1.467 (3) | N3—H3A | 0.9496 |
C5—C9 | 1.381 (3) | O1—H1 | 0.9405 |
C5—C6 | 1.388 (3) | O1—H2 | 0.9102 |
| | | |
C2—C1—H1A | 109.5 | C7—C6—C5 | 119.5 (2) |
C2—C1—H1B | 109.5 | C7—C6—H6 | 120.2 |
H1A—C1—H1B | 109.5 | C5—C6—H6 | 120.2 |
C2—C1—H1C | 109.5 | N1—C7—C6 | 124.0 (2) |
H1A—C1—H1C | 109.5 | N1—C7—H7 | 118.0 |
H1B—C1—H1C | 109.5 | C6—C7—H7 | 118.0 |
N3—C2—C3 | 105.92 (19) | N1—C8—C9 | 123.6 (2) |
N3—C2—C1 | 121.4 (2) | N1—C8—H8 | 118.2 |
C3—C2—C1 | 132.6 (2) | C9—C8—H8 | 118.2 |
C2—C3—C4 | 105.99 (19) | C5—C9—C8 | 119.9 (2) |
C2—C3—H3 | 127.0 | C5—C9—H9 | 120.1 |
C4—C3—H3 | 127.0 | C8—C9—H9 | 120.1 |
N2—C4—C3 | 110.69 (18) | C8—N1—C7 | 116.2 (2) |
N2—C4—C5 | 120.46 (19) | C4—N2—N3 | 104.67 (17) |
C3—C4—C5 | 128.82 (19) | C2—N3—N2 | 112.72 (17) |
C9—C5—C6 | 116.7 (2) | C2—N3—H3A | 126.3 |
C9—C5—C4 | 122.1 (2) | N2—N3—H3A | 120.4 |
C6—C5—C4 | 121.2 (2) | H1—O1—H2 | 107.3 |
| | | |
N3—C2—C3—C4 | 0.6 (3) | C6—C5—C9—C8 | −2.4 (3) |
C1—C2—C3—C4 | −178.3 (2) | C4—C5—C9—C8 | 176.4 (2) |
C2—C3—C4—N2 | −0.7 (3) | N1—C8—C9—C5 | 1.0 (4) |
C2—C3—C4—C5 | 177.0 (2) | C9—C8—N1—C7 | 0.7 (3) |
N2—C4—C5—C9 | 26.6 (3) | C6—C7—N1—C8 | −0.9 (4) |
C3—C4—C5—C9 | −150.9 (2) | C3—C4—N2—N3 | 0.5 (2) |
N2—C4—C5—C6 | −154.6 (2) | C5—C4—N2—N3 | −177.46 (18) |
C3—C4—C5—C6 | 27.8 (3) | C3—C2—N3—N2 | −0.3 (3) |
C9—C5—C6—C7 | 2.2 (3) | C1—C2—N3—N2 | 178.7 (2) |
C4—C5—C6—C7 | −176.6 (2) | C4—N2—N3—C2 | −0.1 (2) |
C5—C6—C7—N1 | −0.5 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1i | 0.95 | 2.55 | 3.450 (3) | 159 |
O1—H2···N2ii | 0.91 | 1.94 | 2.844 (3) | 170 |
N3—H3A···O1iii | 0.95 | 1.77 | 2.724 (2) | 178 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, y−1/2, −z+1/2; (iii) x, −y+1/2, z−1/2. |