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The title compound, C9H13NO, is the key intermediate for the synthesis of the antidiabetic drug pioglitazone and it is used as a versatile intermediate in the synthesis of a number of biologically active novel heterocycles. Both side-chains are located on the same side of the aromatic ring. The mol­ecules are connected by O—H...N hydrogen bonds into ribbons which show a herring-bone-like pattern.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001947/nc6018sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001947/nc6018Isup2.hkl
Contains datablock I

CCDC reference: 264097

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.028
  • wR factor = 0.070
  • Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.65 From the CIF: _reflns_number_total 925 Count of symmetry unique reflns 950 Completeness (_total/calc) 97.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 1 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

2-(5-Ethylpyridin-2-yl)ethanol top
Crystal data top
C9H13NODx = 1.162 Mg m3
Mr = 151.20Mo Kα radiation, λ = 0.71073 Å
Tetragonal, P421cCell parameters from 3889 reflections
Hall symbol: P -4 2nθ = 3.8–25.7°
a = 14.692 (2) ŵ = 0.08 mm1
c = 8.0106 (13) ÅT = 173 K
V = 1729.1 (4) Å3Block, colourless
Z = 80.26 × 0.22 × 0.19 mm
F(000) = 656
Data collection top
Stoe IPDS-II two-circle
diffractometer
777 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 25.7°, θmin = 3.8°
ω scansh = 1715
4259 measured reflectionsk = 1713
925 independent reflectionsl = 69
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)] = 0.028H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070 w = 1/[σ2(Fo2) + (0.0444P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
925 reflectionsΔρmax = 0.11 e Å3
105 parametersΔρmin = 0.10 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.012 (2)
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
xyzUiso*/Ueq
N10.50222 (10)0.18231 (9)0.6445 (2)0.0325 (3)
C20.45565 (12)0.19987 (11)0.7862 (3)0.0316 (4)
C30.37998 (12)0.25661 (12)0.7846 (3)0.0356 (4)
H30.34790.26870.88520.043*
C40.35137 (12)0.29557 (13)0.6362 (3)0.0355 (5)
H40.29970.33450.63480.043*
C50.39814 (12)0.27774 (12)0.4900 (3)0.0320 (4)
C60.47325 (12)0.22022 (12)0.5020 (2)0.0328 (4)
H60.50600.20700.40270.039*
C210.49112 (14)0.15698 (13)0.9441 (3)0.0359 (5)
H21A0.51090.09390.92030.043*
H21B0.44160.15431.02780.043*
C220.57105 (12)0.21068 (12)1.0158 (3)0.0336 (4)
H22A0.62170.21030.93420.040*
H22B0.55210.27471.03270.040*
O230.60249 (10)0.17490 (9)1.16930 (18)0.0383 (4)
H230.6230 (18)0.119 (2)1.153 (4)0.065 (7)*
C510.37158 (12)0.31855 (13)0.3243 (3)0.0392 (5)
H51A0.30580.33310.32570.047*
H51B0.38210.27320.23500.047*
C520.42538 (14)0.40502 (14)0.2843 (3)0.0458 (5)
H52A0.40620.42880.17560.069*
H52B0.49050.39080.28120.069*
H52C0.41380.45080.37070.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0306 (7)0.0345 (7)0.0323 (8)0.0011 (6)0.0006 (7)0.0016 (7)
C20.0305 (8)0.0314 (8)0.0330 (10)0.0054 (7)0.0003 (8)0.0008 (8)
C30.0310 (8)0.0407 (10)0.0351 (12)0.0006 (7)0.0065 (8)0.0020 (8)
C40.0267 (8)0.0368 (9)0.0430 (13)0.0019 (7)0.0004 (8)0.0002 (8)
C50.0294 (8)0.0308 (8)0.0360 (11)0.0046 (6)0.0044 (8)0.0016 (8)
C60.0320 (9)0.0373 (9)0.0292 (11)0.0007 (7)0.0014 (8)0.0046 (8)
C210.0381 (10)0.0357 (9)0.0340 (11)0.0030 (8)0.0002 (9)0.0039 (8)
C220.0381 (9)0.0327 (9)0.0299 (11)0.0018 (6)0.0011 (8)0.0009 (8)
O230.0518 (8)0.0357 (7)0.0272 (8)0.0090 (6)0.0041 (6)0.0031 (6)
C510.0361 (9)0.0417 (10)0.0397 (13)0.0009 (7)0.0071 (9)0.0024 (9)
C520.0484 (11)0.0445 (11)0.0446 (15)0.0028 (9)0.0050 (10)0.0086 (10)
Geometric parameters (Å, º) top
N1—C61.339 (2)C21—H21A0.9900
N1—C21.350 (2)C21—H21B0.9900
C2—C31.390 (3)C22—O231.415 (3)
C2—C211.506 (3)C22—H22A0.9900
C3—C41.385 (3)C22—H22B0.9900
C3—H30.9500O23—H230.88 (3)
C4—C51.382 (3)C51—C521.530 (3)
C4—H40.9500C51—H51A0.9900
C5—C61.393 (2)C51—H51B0.9900
C5—C511.508 (3)C52—H52A0.9800
C6—H60.9500C52—H52B0.9800
C21—C221.527 (3)C52—H52C0.9800
C6—N1—C2118.42 (15)H21A—C21—H21B108.0
N1—C2—C3120.83 (19)O23—C22—C21112.72 (15)
N1—C2—C21116.79 (16)O23—C22—H22A109.0
C3—C2—C21122.36 (19)C21—C22—H22A109.0
C4—C3—C2119.89 (19)O23—C22—H22B109.0
C4—C3—H3120.1C21—C22—H22B109.0
C2—C3—H3120.1H22A—C22—H22B107.8
C5—C4—C3119.86 (17)C22—O23—H23109 (2)
C5—C4—H4120.1C5—C51—C52112.36 (16)
C3—C4—H4120.1C5—C51—H51A109.1
C4—C5—C6116.77 (19)C52—C51—H51A109.1
C4—C5—C51122.79 (16)C5—C51—H51B109.1
C6—C5—C51120.44 (18)C52—C51—H51B109.1
N1—C6—C5124.23 (18)H51A—C51—H51B107.9
N1—C6—H6117.9C51—C52—H52A109.5
C5—C6—H6117.9C51—C52—H52B109.5
C2—C21—C22111.47 (16)H52A—C52—H52B109.5
C2—C21—H21A109.3C51—C52—H52C109.5
C22—C21—H21A109.3H52A—C52—H52C109.5
C2—C21—H21B109.3H52B—C52—H52C109.5
C22—C21—H21B109.3
C6—N1—C2—C30.6 (2)C4—C5—C6—N10.3 (3)
C6—N1—C2—C21179.21 (16)C51—C5—C6—N1178.95 (16)
N1—C2—C3—C40.3 (3)N1—C2—C21—C2280.3 (2)
C21—C2—C3—C4178.79 (17)C3—C2—C21—C2298.2 (2)
C2—C3—C4—C50.1 (3)C2—C21—C22—O23176.65 (16)
C3—C4—C5—C60.1 (3)C4—C5—C51—C5295.2 (2)
C3—C4—C5—C51179.29 (17)C6—C5—C51—C5284.0 (2)
C2—N1—C6—C50.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O23—H23···N1i0.88 (3)1.93 (3)2.802 (2)171 (3)
Symmetry code: (i) y+1/2, x1/2, z+1/2.
 

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