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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)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019027/ac2029sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019027/ac2029Isup2.hkl
Contains datablock I

CCDC reference: 610682

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

Computing details top

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 top
Crystal data top
C14H11N3OF(000) = 496
Mr = 237.26Dx = 1.397 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5145 reflections
a = 9.618 (2) Åθ = 2.5–35°
b = 10.538 (2) ŵ = 0.09 mm1
c = 11.482 (3) ÅT = 120 K
β = 104.215 (10)°Parallelepiped, light yellow
V = 1128.1 (4) Å30.40 × 0.33 × 0.25 mm
Z = 4
Data collection top
Nonius KappaCCD (with an Oxford Cryosystems Cryostream cooler)
diffractometer
Rint = 0.070
ω scans with κ offsetsθmax = 35.1°, θmin = 2.7°
9591 measured reflectionsh = 1515
4948 independent reflectionsk = 1616
2653 reflections with I > 2σ(I)l = 1818
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.052 w = 1/[σ2(Fo2) + (0.0609P)2]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.136(Δ/σ)max < 0.001
S = 0.98Δρmax = 0.40 e Å3
4948 reflectionsΔρmin = 0.29 e Å3
167 parameters
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.15296 (12)0.63701 (10)0.48304 (11)0.0178 (2)
C20.20653 (12)0.63127 (11)0.38389 (11)0.0189 (2)
H20.20000.69400.32340.023*
C30.27423 (13)0.51099 (10)0.39094 (11)0.0174 (2)
C40.35370 (12)0.45742 (10)0.30747 (11)0.0177 (2)
C50.32238 (13)0.49448 (12)0.18727 (11)0.0210 (3)
H50.24740.55360.15790.025*
C60.40009 (14)0.44560 (12)0.11005 (12)0.0252 (3)
H60.37840.47170.02840.030*
C70.50896 (13)0.35893 (12)0.15228 (12)0.0262 (3)
H70.56250.32590.09980.031*
C80.53987 (13)0.32026 (12)0.27177 (12)0.0250 (3)
H80.61360.25980.30040.030*
C90.46338 (13)0.36962 (11)0.34904 (12)0.0215 (3)
H90.48570.34360.43070.026*
C100.15810 (12)0.48960 (11)0.65421 (10)0.0170 (2)
C110.20234 (13)0.37338 (11)0.70941 (11)0.0203 (2)
H110.25290.31330.67380.024*
C120.16977 (13)0.34932 (12)0.81752 (11)0.0224 (3)
H120.19840.27160.85830.027*
C130.09485 (13)0.43908 (11)0.86709 (11)0.0215 (3)
H130.07130.42350.94140.026*
C140.05564 (13)0.55112 (11)0.80584 (11)0.0204 (3)
H140.00460.61240.83960.024*
N10.18654 (11)0.52358 (9)0.54453 (9)0.0176 (2)
N20.26278 (11)0.44475 (9)0.48705 (9)0.0188 (2)
N30.08650 (10)0.57735 (9)0.70043 (9)0.0193 (2)
O10.08103 (10)0.72925 (8)0.52351 (8)0.0242 (2)
H1O0.0605 (19)0.6930 (16)0.5993 (17)0.063 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0191 (5)0.0154 (5)0.0196 (6)0.0004 (4)0.0058 (5)0.0001 (4)
C20.0217 (6)0.0173 (5)0.0185 (6)0.0002 (5)0.0068 (5)0.0016 (4)
C30.0183 (5)0.0167 (5)0.0179 (6)0.0017 (5)0.0058 (5)0.0014 (4)
C40.0165 (5)0.0178 (5)0.0196 (6)0.0020 (4)0.0057 (5)0.0019 (4)
C50.0204 (6)0.0218 (6)0.0214 (7)0.0008 (5)0.0061 (5)0.0004 (5)
C60.0243 (6)0.0330 (7)0.0192 (6)0.0039 (6)0.0074 (5)0.0020 (5)
C70.0233 (6)0.0288 (7)0.0295 (8)0.0025 (5)0.0126 (6)0.0084 (5)
C80.0216 (6)0.0235 (6)0.0308 (8)0.0025 (5)0.0082 (5)0.0024 (5)
C90.0214 (6)0.0211 (6)0.0220 (6)0.0011 (5)0.0056 (5)0.0011 (5)
C100.0179 (5)0.0182 (5)0.0154 (6)0.0019 (4)0.0049 (5)0.0010 (4)
C110.0227 (6)0.0188 (6)0.0203 (6)0.0022 (5)0.0070 (5)0.0012 (4)
C120.0256 (6)0.0195 (6)0.0227 (7)0.0004 (5)0.0069 (5)0.0029 (4)
C130.0247 (6)0.0231 (6)0.0180 (6)0.0026 (5)0.0079 (5)0.0006 (4)
C140.0214 (6)0.0214 (6)0.0199 (6)0.0027 (5)0.0080 (5)0.0032 (4)
N10.0210 (5)0.0165 (5)0.0168 (5)0.0021 (4)0.0074 (4)0.0008 (4)
N20.0216 (5)0.0175 (5)0.0196 (5)0.0016 (4)0.0093 (4)0.0016 (4)
N30.0213 (5)0.0189 (5)0.0190 (5)0.0011 (4)0.0073 (4)0.0007 (4)
O10.0319 (5)0.0188 (4)0.0255 (5)0.0065 (4)0.0138 (4)0.0020 (3)
Geometric parameters (Å, º) top
C1—O11.3406 (13)C8—H80.95
C1—C21.3614 (17)C9—H90.95
C1—N11.3855 (14)C10—N31.3381 (15)
C2—C31.4182 (16)C10—C111.3965 (16)
C2—H20.95C10—N11.3994 (15)
C3—N21.3330 (15)C11—C121.3764 (16)
C3—C41.4769 (16)C11—H110.95
C4—C51.3942 (17)C12—C131.3926 (17)
C4—C91.3962 (17)C12—H120.95
C5—C61.3913 (17)C13—C141.3785 (17)
C5—H50.95C13—H130.95
C6—C71.3843 (19)C14—N31.3438 (15)
C6—H60.95C14—H140.95
C7—C81.3916 (18)N1—N21.3787 (13)
C7—H70.95O1—H1O1.013 (18)
C8—C91.3854 (17)
O1—C1—C2130.96 (11)C8—C9—C4120.35 (12)
O1—C1—N1121.64 (10)C8—C9—H9119.8
C2—C1—N1107.40 (10)C4—C9—H9119.8
C1—C2—C3104.76 (10)N3—C10—C11123.72 (11)
C1—C2—H2127.6N3—C10—N1114.42 (10)
C3—C2—H2127.6C11—C10—N1121.85 (10)
N2—C3—C2112.65 (10)C12—C11—C10117.35 (11)
N2—C3—C4119.88 (10)C12—C11—H11121.3
C2—C3—C4127.45 (10)C10—C11—H11121.3
C5—C4—C9119.04 (11)C11—C12—C13119.91 (12)
C5—C4—C3120.99 (11)C11—C12—H12120
C9—C4—C3119.96 (11)C13—C12—H12120
C6—C5—C4120.52 (12)C14—C13—C12118.52 (12)
C6—C5—H5119.7C14—C13—H13120.7
C4—C5—H5119.7C12—C13—H13120.7
C7—C6—C5119.97 (12)N3—C14—C13122.85 (11)
C7—C6—H6120N3—C14—H14118.6
C5—C6—H6120C13—C14—H14118.6
C6—C7—C8119.91 (12)N2—N1—C1111.15 (9)
C6—C7—H7120N2—N1—C10121.40 (9)
C8—C7—H7120C1—N1—C10127.35 (9)
C9—C8—C7120.19 (12)C3—N2—N1104.03 (9)
C9—C8—H8119.9C10—N3—C14117.65 (10)
C7—C8—H8119.9C1—O1—H1O104.5 (10)
O1—C1—C2—C3178.69 (12)C10—C11—C12—C130.33 (18)
N1—C1—C2—C30.78 (13)C11—C12—C13—C140.31 (19)
C1—C2—C3—N20.69 (14)C12—C13—C14—N30.04 (19)
C1—C2—C3—C4178.06 (11)O1—C1—N1—N2178.87 (10)
N2—C3—C4—C5153.98 (11)C2—C1—N1—N20.67 (14)
C2—C3—C4—C527.35 (18)O1—C1—N1—C102.45 (19)
N2—C3—C4—C926.92 (17)C2—C1—N1—C10177.08 (11)
C2—C3—C4—C9151.75 (12)N3—C10—N1—N2178.23 (10)
C9—C4—C5—C60.58 (18)C11—C10—N1—N21.52 (17)
C3—C4—C5—C6178.53 (11)N3—C10—N1—C12.15 (17)
C4—C5—C6—C70.36 (19)C11—C10—N1—C1177.61 (11)
C5—C6—C7—C80.40 (19)C2—C3—N2—N10.29 (13)
C6—C7—C8—C90.93 (19)C4—C3—N2—N1178.57 (10)
C7—C8—C9—C40.71 (19)C1—N1—N2—C30.23 (13)
C5—C4—C9—C80.04 (17)C10—N1—N2—C3176.89 (10)
C3—C4—C9—C8179.07 (11)C11—C10—N3—C140.17 (18)
N3—C10—C11—C120.09 (18)N1—C10—N3—C14179.92 (10)
N1—C10—C11—C12179.64 (11)C13—C14—N3—C100.19 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···N31.013 (18)1.659 (18)2.5767 (14)148.3 (15)
 

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