3-Phenyl-1-(2-pyrid­yl)-1H-pyrazol-5-ol

In the title compound, C₁₄H₁₁N₃O, there is an intra­molecular O—H...N hydrogen bond enforcing coplanarity of the pyrazole and pyridine rings, with O—H = 1.013 (18) Å, H...N = 1.659 (18) Å, O...N = 2.5767 (14) Å, and O—H...N = 148.3 (15)°.

Key indicators

• Single-crystal X-ray study
• T = 120 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.052
• wR factor = 0.136
• Data-to-parameter ratio = 29.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H1O    ...       1.01 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3-Phenyl-1-(2-pyridyl)-1H-pyrazol-5-ol

Crystal data

C14H11N3O	F(000) = 496
Mr = 237.26	Dx = 1.397 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5145 reflections
a = 9.618 (2) Å	θ = 2.5–35°
b = 10.538 (2) Å	µ = 0.09 mm^−1
c = 11.482 (3) Å	T = 120 K
β = 104.215 (10)°	Parallelepiped, light yellow
V = 1128.1 (4) Å^3	0.40 × 0.33 × 0.25 mm
Z = 4

Data collection

Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler) diffractometer	Rint = 0.070
ω scans with κ offsets	θmax = 35.1°, θmin = 2.7°
9591 measured reflections	h = −15→15
4948 independent reflections	k = −16→16
2653 reflections with I > 2σ(I)	l = −18→18

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(Fo^2) + (0.0609P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.136	(Δ/σ)max < 0.001
S = 0.98	Δρmax = 0.40 e Å^−3
4948 reflections	Δρmin = −0.29 e Å^−3
167 parameters

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.15296 (12)	0.63701 (10)	0.48304 (11)	0.0178 (2)
C2	0.20653 (12)	0.63127 (11)	0.38389 (11)	0.0189 (2)
H2	0.2000	0.6940	0.3234	0.023*
C3	0.27423 (13)	0.51099 (10)	0.39094 (11)	0.0174 (2)
C4	0.35370 (12)	0.45742 (10)	0.30747 (11)	0.0177 (2)
C5	0.32238 (13)	0.49448 (12)	0.18727 (11)	0.0210 (3)
H5	0.2474	0.5536	0.1579	0.025*
C6	0.40009 (14)	0.44560 (12)	0.11005 (12)	0.0252 (3)
H6	0.3784	0.4717	0.0284	0.030*
C7	0.50896 (13)	0.35893 (12)	0.15228 (12)	0.0262 (3)
H7	0.5625	0.3259	0.0998	0.031*
C8	0.53987 (13)	0.32026 (12)	0.27177 (12)	0.0250 (3)
H8	0.6136	0.2598	0.3004	0.030*
C9	0.46338 (13)	0.36962 (11)	0.34904 (12)	0.0215 (3)
H9	0.4857	0.3436	0.4307	0.026*
C10	0.15810 (12)	0.48960 (11)	0.65421 (10)	0.0170 (2)
C11	0.20234 (13)	0.37338 (11)	0.70941 (11)	0.0203 (2)
H11	0.2529	0.3133	0.6738	0.024*
C12	0.16977 (13)	0.34932 (12)	0.81752 (11)	0.0224 (3)
H12	0.1984	0.2716	0.8583	0.027*
C13	0.09485 (13)	0.43908 (11)	0.86709 (11)	0.0215 (3)
H13	0.0713	0.4235	0.9414	0.026*
C14	0.05564 (13)	0.55112 (11)	0.80584 (11)	0.0204 (3)
H14	0.0046	0.6124	0.8396	0.024*
N1	0.18654 (11)	0.52358 (9)	0.54453 (9)	0.0176 (2)
N2	0.26278 (11)	0.44475 (9)	0.48705 (9)	0.0188 (2)
N3	0.08650 (10)	0.57735 (9)	0.70043 (9)	0.0193 (2)
O1	0.08103 (10)	0.72925 (8)	0.52351 (8)	0.0242 (2)
H1O	0.0605 (19)	0.6930 (16)	0.5993 (17)	0.063 (6)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0191 (5)	0.0154 (5)	0.0196 (6)	0.0004 (4)	0.0058 (5)	−0.0001 (4)
C2	0.0217 (6)	0.0173 (5)	0.0185 (6)	−0.0002 (5)	0.0068 (5)	0.0016 (4)
C3	0.0183 (5)	0.0167 (5)	0.0179 (6)	−0.0017 (5)	0.0058 (5)	−0.0014 (4)
C4	0.0165 (5)	0.0178 (5)	0.0196 (6)	−0.0020 (4)	0.0057 (5)	−0.0019 (4)
C5	0.0204 (6)	0.0218 (6)	0.0214 (7)	−0.0008 (5)	0.0061 (5)	−0.0004 (5)
C6	0.0243 (6)	0.0330 (7)	0.0192 (6)	−0.0039 (6)	0.0074 (5)	−0.0020 (5)
C7	0.0233 (6)	0.0288 (7)	0.0295 (8)	−0.0025 (5)	0.0126 (6)	−0.0084 (5)
C8	0.0216 (6)	0.0235 (6)	0.0308 (8)	0.0025 (5)	0.0082 (5)	−0.0024 (5)
C9	0.0214 (6)	0.0211 (6)	0.0220 (6)	−0.0011 (5)	0.0056 (5)	−0.0011 (5)
C10	0.0179 (5)	0.0182 (5)	0.0154 (6)	−0.0019 (4)	0.0049 (5)	−0.0010 (4)
C11	0.0227 (6)	0.0188 (6)	0.0203 (6)	0.0022 (5)	0.0070 (5)	0.0012 (4)
C12	0.0256 (6)	0.0195 (6)	0.0227 (7)	−0.0004 (5)	0.0069 (5)	0.0029 (4)
C13	0.0247 (6)	0.0231 (6)	0.0180 (6)	−0.0026 (5)	0.0079 (5)	0.0006 (4)
C14	0.0214 (6)	0.0214 (6)	0.0199 (6)	−0.0027 (5)	0.0080 (5)	−0.0032 (4)
N1	0.0210 (5)	0.0165 (5)	0.0168 (5)	0.0021 (4)	0.0074 (4)	0.0008 (4)
N2	0.0216 (5)	0.0175 (5)	0.0196 (5)	0.0016 (4)	0.0093 (4)	−0.0016 (4)
N3	0.0213 (5)	0.0189 (5)	0.0190 (5)	−0.0011 (4)	0.0073 (4)	−0.0007 (4)
O1	0.0319 (5)	0.0188 (4)	0.0255 (5)	0.0065 (4)	0.0138 (4)	0.0020 (3)

Geometric parameters (Å, º)

C1—O1	1.3406 (13)	C8—H8	0.95
C1—C2	1.3614 (17)	C9—H9	0.95
C1—N1	1.3855 (14)	C10—N3	1.3381 (15)
C2—C3	1.4182 (16)	C10—C11	1.3965 (16)
C2—H2	0.95	C10—N1	1.3994 (15)
C3—N2	1.3330 (15)	C11—C12	1.3764 (16)
C3—C4	1.4769 (16)	C11—H11	0.95
C4—C5	1.3942 (17)	C12—C13	1.3926 (17)
C4—C9	1.3962 (17)	C12—H12	0.95
C5—C6	1.3913 (17)	C13—C14	1.3785 (17)
C5—H5	0.95	C13—H13	0.95
C6—C7	1.3843 (19)	C14—N3	1.3438 (15)
C6—H6	0.95	C14—H14	0.95
C7—C8	1.3916 (18)	N1—N2	1.3787 (13)
C7—H7	0.95	O1—H1O	1.013 (18)
C8—C9	1.3854 (17)
O1—C1—C2	130.96 (11)	C8—C9—C4	120.35 (12)
O1—C1—N1	121.64 (10)	C8—C9—H9	119.8
C2—C1—N1	107.40 (10)	C4—C9—H9	119.8
C1—C2—C3	104.76 (10)	N3—C10—C11	123.72 (11)
C1—C2—H2	127.6	N3—C10—N1	114.42 (10)
C3—C2—H2	127.6	C11—C10—N1	121.85 (10)
N2—C3—C2	112.65 (10)	C12—C11—C10	117.35 (11)
N2—C3—C4	119.88 (10)	C12—C11—H11	121.3
C2—C3—C4	127.45 (10)	C10—C11—H11	121.3
C5—C4—C9	119.04 (11)	C11—C12—C13	119.91 (12)
C5—C4—C3	120.99 (11)	C11—C12—H12	120
C9—C4—C3	119.96 (11)	C13—C12—H12	120
C6—C5—C4	120.52 (12)	C14—C13—C12	118.52 (12)
C6—C5—H5	119.7	C14—C13—H13	120.7
C4—C5—H5	119.7	C12—C13—H13	120.7
C7—C6—C5	119.97 (12)	N3—C14—C13	122.85 (11)
C7—C6—H6	120	N3—C14—H14	118.6
C5—C6—H6	120	C13—C14—H14	118.6
C6—C7—C8	119.91 (12)	N2—N1—C1	111.15 (9)
C6—C7—H7	120	N2—N1—C10	121.40 (9)
C8—C7—H7	120	C1—N1—C10	127.35 (9)
C9—C8—C7	120.19 (12)	C3—N2—N1	104.03 (9)
C9—C8—H8	119.9	C10—N3—C14	117.65 (10)
C7—C8—H8	119.9	C1—O1—H1O	104.5 (10)
O1—C1—C2—C3	178.69 (12)	C10—C11—C12—C13	0.33 (18)
N1—C1—C2—C3	−0.78 (13)	C11—C12—C13—C14	−0.31 (19)
C1—C2—C3—N2	0.69 (14)	C12—C13—C14—N3	0.04 (19)
C1—C2—C3—C4	−178.06 (11)	O1—C1—N1—N2	−178.87 (10)
N2—C3—C4—C5	153.98 (11)	C2—C1—N1—N2	0.67 (14)
C2—C3—C4—C5	−27.35 (18)	O1—C1—N1—C10	−2.45 (19)
N2—C3—C4—C9	−26.92 (17)	C2—C1—N1—C10	177.08 (11)
C2—C3—C4—C9	151.75 (12)	N3—C10—N1—N2	178.23 (10)
C9—C4—C5—C6	−0.58 (18)	C11—C10—N1—N2	−1.52 (17)
C3—C4—C5—C6	178.53 (11)	N3—C10—N1—C1	2.15 (17)
C4—C5—C6—C7	0.36 (19)	C11—C10—N1—C1	−177.61 (11)
C5—C6—C7—C8	0.40 (19)	C2—C3—N2—N1	−0.29 (13)
C6—C7—C8—C9	−0.93 (19)	C4—C3—N2—N1	178.57 (10)
C7—C8—C9—C4	0.71 (19)	C1—N1—N2—C3	−0.23 (13)
C5—C4—C9—C8	0.04 (17)	C10—N1—N2—C3	−176.89 (10)
C3—C4—C9—C8	−179.07 (11)	C11—C10—N3—C14	−0.17 (18)
N3—C10—C11—C12	−0.09 (18)	N1—C10—N3—C14	−179.92 (10)
N1—C10—C11—C12	179.64 (11)	C13—C14—N3—C10	0.19 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N3	1.013 (18)	1.659 (18)	2.5767 (14)	148.3 (15)