4-(5-Methyl-1H-pyrazol-3-yl)pyridine monohydrate

In the title mol­ecule, C₉H₉N₃·H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](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

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Computing details

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-1H-pyrazol-3-yl)pyridine monohydrate

Crystal data

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) Å^3	0.28 × 0.14 × 0.12 mm
Z = 4

Data collection

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

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0596P)^2] where P = (Fo^2 + 2Fc^2)/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

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
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1^i	0.95	2.55	3.450 (3)	159
O1—H2···N2^ii	0.91	1.94	2.844 (3)	170
N3—H3A···O1^iii	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.