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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3196
https://doi.org/10.1107/S160053681004643X

1-Butyl-4-hy­dr­oxy-3-methyl­quinoline-2(1H)-one

Zuzana Kozubková,a Marek Nečasb and Robert Víchaa*

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
*Correspondence e-mail: rvicha@ft.utb.cz

(Received 8 November 2010; accepted 10 November 2010; online 17 November 2010)

In the crystal of the title compound, C14H17NO2, mol­ecules are arranged into chains along the b axis linked via O—H⋯O hydrogen bonds. While the benzene ring is essentially planar, with a maximum deviation from the best plane of 0.003 (1) Å, the pyridine ring is slightly V-shaped: the distance of the carbonyl C atom from the benzene best plane is 0.120 (1) Å. The hy­droxy group is inclined markedly towards the benzene ring reducing the C—C—O bond angle to 113.21 (10)°.

Related literature

For the preparation, see: Stadlbauer & Kappe (1985[Stadlbauer, W. & Kappe, T. (1985). Monatsch. Chem. 116, 1005-1015.]). The title compound is a member of a group of substituted 4-hy­droxy­quinoline-2-ones used for preparation of new classes of heterocyclic systems, see: Klásek et al. (1998[Klásek, A., Kafka, S., Polis, J. & Košmrlj, J. (1998). Heterocycles, 48, 2309-2326.]); Kafka et al. (2002[Kafka, S., Klásek, A., Polis, J. & Košmrlj, J. (2002). Heterocycles, 57, 1659-1682.]).

[Scheme 1]

Experimental

Crystal data

  • C14H17NO2

  • Mr = 231.29

  • Monoclinic, P 21 /c

  • a = 11.8576 (7) Å

  • b = 10.7790 (6) Å

  • c = 9.8835 (7) Å

  • β = 110.749 (7)°

  • V = 1181.31 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 120 K

  • 0.40 × 0.40 × 0.40 mm
Data collection

  • Oxford Diffraction Xcalibur diffractometer with a Sapphire2 detector

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.978, Tmax = 1.000

  • 4533 measured reflections

  • 2077 independent reflections

  • 1625 reflections with I > 2σ(I)

  • Rint = 0.011
Refinement

  • R[F2 > 2σ(F2)] = 0.033

  • wR(F2) = 0.086

  • S = 0.99

  • 2077 reflections

  • 157 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O2—H2A⋯O1i 0.84 1.86 2.6529 (14) 156
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053681004643X/zl2326sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681004643X/zl2326Isup2.hkl

checkCIF report


Comment top

Quinoline derivatives are well known and extensively studied especially for their wide occurance in nature and for their rich spectrum of biological activities. The title compound is a member of the group of substituted 4-hydroxyquinoline-2-ones used for preparation of new classes of heterocyclic systems (Klásek et al., 1998; Kafka et al., 2002).

The molecule of the title compound (Fig. 1) consists of fused benzene and pyridine rings. The benzene ring is essentially planar with a maximum deviation from the best plane of 0.0026 (12)Å for C6. The pyridine ring is slightly bent along the N1—C3 line with torsion angles C9—N1—C1—C2 and C4—C3—C2—C1 being 5.79 (17) and -6.38 (18)°, respectively. The geometry around C3 markedly differs from the ideal pattern for a sp2 carbon. All involved atoms C4–C2 and O1 lie in the plane of the phenyl ring (maximum deviation from the best plane is 0.0083 (12)Å for C3) but the valence angles C4—C3—O1 and C2—C3—O1 are 113.21 (10) and 125.91 (11)°. Molecules are linked via O2—H2···O1 H-bonds (Fig. 2, Table 1) into chains parallel to the b-axis.

Related literature top

For the preparation, see: Stadlbauer & Kappe (1985).The title compound is a member of a group of substituted 4-hydroxyquinoline-2-ones used for preparation of new classes of heterocyclic systems, see: Klásek et al. (1998); Kafka et al. (2002).

Experimental top

Title compound was prepared according to a slightly modified procedure published by Stadlbauer & Kappe (1985). A mixture of N-butylaniline (16 cm3, 0.1 mol) and diethyl methylmalonate (17.2 cm3, 0.1 mol) was gradually heated in a Wood's metal bath at 413–553K for 6 h. The reaction was stopped when the amount of condensed ethanol reaches about 93% of the theoretical value. The hot mixture was poured on a metal plate and the crude product was quantitatively transferred into a 500 cm3 Erlenmeyer flask. After addition of 300 cm3 of 0.5 M NaOH and 50 cm3 of toluene the resulting mixture was stirred for 1 h. The suspension was extracted twice with 40 cm3 of toluene and the collected organic portions were treated with powdered activated carbon for 30 min at room temperature. The activated carbon was filtered off and approximately 300–400 cm3 of 5% HCl was added gradually into the filtrate. The precipitated crude product were filtered with suction and washed with water until neutral pH. Single crystals for X-ray analysis were grown by spontaneous evaporation from deuterochloroform at room temperature.

Refinement top

Hydrogen atoms were positioned geometrically and refined as riding using standard SHELXL-97 facilities, with their Uiso set to either 1.2Ueq or 1.5Ueq(methyl) of their parent atoms.

Structure description top

Quinoline derivatives are well known and extensively studied especially for their wide occurance in nature and for their rich spectrum of biological activities. The title compound is a member of the group of substituted 4-hydroxyquinoline-2-ones used for preparation of new classes of heterocyclic systems (Klásek et al., 1998; Kafka et al., 2002).

The molecule of the title compound (Fig. 1) consists of fused benzene and pyridine rings. The benzene ring is essentially planar with a maximum deviation from the best plane of 0.0026 (12)Å for C6. The pyridine ring is slightly bent along the N1—C3 line with torsion angles C9—N1—C1—C2 and C4—C3—C2—C1 being 5.79 (17) and -6.38 (18)°, respectively. The geometry around C3 markedly differs from the ideal pattern for a sp2 carbon. All involved atoms C4–C2 and O1 lie in the plane of the phenyl ring (maximum deviation from the best plane is 0.0083 (12)Å for C3) but the valence angles C4—C3—O1 and C2—C3—O1 are 113.21 (10) and 125.91 (11)°. Molecules are linked via O2—H2···O1 H-bonds (Fig. 2, Table 1) into chains parallel to the b-axis.

For the preparation, see: Stadlbauer & Kappe (1985).The title compound is a member of a group of substituted 4-hydroxyquinoline-2-ones used for preparation of new classes of heterocyclic systems, see: Klásek et al. (1998); Kafka et al. (2002).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement view of the asymmetric unit with atoms represented as 50% probability ellipsoids.
[Figure 2] Fig. 2. Part of the crystal structure showing chains linked via O—H···O hydrogen bonds along the b-axis. H-atoms have been omitted except for those participating in H-bonds. Symmetry code: (i) -x + 1, y + 1/2, -z + 1/2.
1-Butyl-4-hydroxy-3-methylquinoline-2(1H)-one top
Crystal data top
C14H17NO2F(000) = 496
Mr = 231.29Dx = 1.300 Mg m−3
Monoclinic, P21/cMelting point: 471 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 11.8576 (7) ÅCell parameters from 2482 reflections
b = 10.7790 (6) Åθ = 3.0–27.6°
c = 9.8835 (7) ŵ = 0.09 mm−1
β = 110.749 (7)°T = 120 K
V = 1181.31 (13) Å3Block, yellow
Z = 40.40 × 0.40 × 0.40 mm
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire2 detector		2077 independent reflections
Radiation source: Enhance (Mo) X-ray Source1625 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.011
Detector resolution: 8.4353 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = −13→14
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		k = −9→12
Tmin = 0.978, Tmax = 1.000l = −11→11
4533 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 0.99 w = 1/[σ2(Fo2) + (0.0533P)2]
where P = (Fo2 + 2Fc2)/3
2077 reflections(Δ/σ)max = 0.001
157 parametersΔρmax = 0.15 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C14H17NO2V = 1181.31 (13) Å3
Mr = 231.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 11.8576 (7) ŵ = 0.09 mm−1
b = 10.7790 (6) ÅT = 120 K
c = 9.8835 (7) Å0.40 × 0.40 × 0.40 mm
β = 110.749 (7)°
Data collection top
Oxford Diffraction Xcalibur
diffractometer with a Sapphire2 detector		2077 independent reflections
Absorption correction: multi-scan
(CrysAlis RED; Oxford Diffraction, 2009)		1625 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 1.000Rint = 0.011
4533 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.086H-atom parameters constrained
S = 0.99Δρmax = 0.15 e Å−3
2077 reflectionsΔρmin = −0.21 e Å−3
157 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.

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 > 2σ(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
O10.58070 (7)0.83511 (7)0.20280 (9)0.0221 (2)
O20.59308 (7)1.27747 (7)0.19762 (9)0.0210 (2)
H2A0.54081.27460.23680.031*
N10.68444 (8)0.93464 (9)0.08212 (10)0.0165 (2)
C10.61444 (10)0.93675 (11)0.16869 (12)0.0168 (3)
C20.58304 (10)1.05481 (11)0.21508 (12)0.0164 (3)
C30.62176 (10)1.16166 (11)0.17139 (12)0.0161 (3)
C40.70374 (10)1.15797 (11)0.09202 (12)0.0166 (3)
C50.75484 (10)1.26662 (11)0.06041 (13)0.0194 (3)
H5A0.73421.34470.08980.023*
C60.83446 (11)1.26165 (12)−0.01253 (13)0.0220 (3)
H6A0.86881.3357−0.03300.026*
C70.86408 (10)1.14718 (12)−0.05593 (13)0.0227 (3)
H7A0.91851.1437−0.10700.027*
C80.81590 (10)1.03880 (11)−0.02618 (13)0.0195 (3)
H8A0.83760.9615−0.05620.023*
C90.73476 (10)1.04230 (11)0.04853 (12)0.0164 (3)
C100.50878 (10)1.05049 (11)0.31107 (13)0.0206 (3)
H10A0.50681.13310.35160.031*
H10B0.54480.99130.38990.031*
H10C0.42641.02430.25420.031*
C110.70685 (10)0.81262 (11)0.02898 (13)0.0183 (3)
H11A0.71450.8233−0.06690.022*
H11B0.63680.75800.01640.022*
C120.82009 (10)0.75039 (12)0.13077 (13)0.0198 (3)
H12A0.80720.72730.22120.024*
H12B0.88770.81030.15610.024*
C130.85459 (11)0.63463 (12)0.06562 (14)0.0251 (3)
H13A0.78490.57730.03320.030*
H13B0.87420.6585−0.02030.030*
C140.96221 (11)0.56796 (11)0.17331 (14)0.0253 (3)
H14A0.98550.49820.12520.038*
H14B0.94050.53690.25400.038*
H14C1.03000.62580.21010.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0251 (5)0.0147 (5)0.0314 (5)−0.0013 (4)0.0161 (4)0.0010 (4)
O20.0232 (5)0.0150 (5)0.0303 (5)0.0007 (4)0.0164 (4)−0.0005 (4)
N10.0173 (5)0.0139 (6)0.0198 (5)−0.0004 (4)0.0085 (4)−0.0015 (4)
C10.0153 (6)0.0165 (7)0.0178 (6)−0.0014 (5)0.0052 (5)0.0013 (5)
C20.0139 (6)0.0178 (7)0.0170 (6)0.0007 (5)0.0047 (5)0.0004 (5)
C30.0153 (6)0.0140 (7)0.0171 (6)0.0015 (5)0.0034 (5)−0.0016 (5)
C40.0146 (6)0.0176 (7)0.0159 (6)0.0005 (5)0.0035 (5)0.0011 (5)
C50.0208 (6)0.0165 (7)0.0201 (7)0.0001 (5)0.0061 (5)0.0007 (5)
C60.0235 (6)0.0205 (7)0.0238 (7)−0.0053 (5)0.0107 (5)0.0026 (6)
C70.0213 (6)0.0279 (8)0.0219 (7)−0.0007 (6)0.0113 (5)0.0017 (6)
C80.0199 (6)0.0201 (7)0.0196 (7)0.0016 (5)0.0082 (5)−0.0021 (5)
C90.0148 (6)0.0177 (7)0.0149 (6)−0.0013 (5)0.0032 (5)0.0011 (5)
C100.0241 (6)0.0156 (7)0.0262 (7)0.0004 (5)0.0138 (5)0.0002 (5)
C110.0207 (6)0.0144 (7)0.0216 (7)−0.0020 (5)0.0096 (5)−0.0037 (5)
C120.0214 (6)0.0176 (7)0.0217 (6)−0.0006 (5)0.0093 (5)−0.0011 (5)
C130.0265 (7)0.0212 (7)0.0262 (7)0.0039 (6)0.0074 (6)−0.0021 (6)
C140.0282 (7)0.0220 (7)0.0271 (7)0.0050 (6)0.0115 (6)0.0017 (6)
Geometric parameters (Å, º) top
O1—C11.2528 (13)C8—C91.4056 (16)
O2—C31.3429 (13)C8—H8A0.9500
O2—H2A0.8400C10—H10A0.9800
N1—C11.3873 (15)C10—H10B0.9800
N1—C91.3976 (14)C10—H10C0.9800
N1—C111.4749 (14)C11—C121.5192 (16)
C1—C21.4454 (16)C11—H11A0.9900
C2—C31.3655 (16)C11—H11B0.9900
C2—C101.5064 (15)C12—C131.5249 (16)
C3—C41.4499 (16)C12—H12A0.9900
C4—C51.4037 (16)C12—H12B0.9900
C4—C91.4095 (15)C13—C141.5217 (16)
C5—C61.3771 (16)C13—H13A0.9900
C5—H5A0.9500C13—H13B0.9900
C6—C71.3915 (17)C14—H14A0.9800
C6—H6A0.9500C14—H14B0.9800
C7—C81.3772 (16)C14—H14C0.9800
C7—H7A0.9500
C3—O2—H2A109.5C2—C10—H10A109.5
C1—N1—C9122.14 (10)C2—C10—H10B109.5
C1—N1—C11117.19 (9)H10A—C10—H10B109.5
C9—N1—C11120.66 (10)C2—C10—H10C109.5
O1—C1—N1118.00 (10)H10A—C10—H10C109.5
O1—C1—C2122.81 (11)H10B—C10—H10C109.5
N1—C1—C2119.19 (10)N1—C11—C12112.73 (9)
C3—C2—C1119.28 (11)N1—C11—H11A109.0
C3—C2—C10124.21 (11)C12—C11—H11A109.0
C1—C2—C10116.51 (10)N1—C11—H11B109.0
O2—C3—C2125.91 (10)C12—C11—H11B109.0
O2—C3—C4113.21 (10)H11A—C11—H11B107.8
C2—C3—C4120.86 (10)C11—C12—C13112.83 (10)
C5—C4—C9119.36 (11)C11—C12—H12A109.0
C5—C4—C3121.50 (11)C13—C12—H12A109.0
C9—C4—C3119.12 (10)C11—C12—H12B109.0
C6—C5—C4120.94 (12)C13—C12—H12B109.0
C6—C5—H5A119.5H12A—C12—H12B107.8
C4—C5—H5A119.5C14—C13—C12112.02 (10)
C5—C6—C7119.38 (11)C14—C13—H13A109.2
C5—C6—H6A120.3C12—C13—H13A109.2
C7—C6—H6A120.3C14—C13—H13B109.2
C8—C7—C6121.15 (11)C12—C13—H13B109.2
C8—C7—H7A119.4H13A—C13—H13B107.9
C6—C7—H7A119.4C13—C14—H14A109.5
C7—C8—C9120.16 (11)C13—C14—H14B109.5
C7—C8—H8A119.9H14A—C14—H14B109.5
C9—C8—H8A119.9C13—C14—H14C109.5
N1—C9—C8122.13 (11)H14A—C14—H14C109.5
N1—C9—C4118.85 (10)H14B—C14—H14C109.5
C8—C9—C4119.02 (11)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.841.862.6529 (14)156
Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC14H17NO2
Mr231.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)120
a, b, c (Å)11.8576 (7), 10.7790 (6), 9.8835 (7)
β (°) 110.749 (7)
V (Å3)1181.31 (13)
Z4
Radiation typeMo Kα
µ (mm−1)0.09
Crystal size (mm)0.40 × 0.40 × 0.40
Data collection
DiffractometerOxford Diffraction Xcalibur
diffractometer with a Sapphire2 detector
Absorption correctionMulti-scan
(CrysAlis RED; Oxford Diffraction, 2009)
Tmin, Tmax0.978, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections		4533, 2077, 1625
Rint0.011
(sin θ/λ)max (Å−1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.086, 0.99
No. of reflections2077
No. of parameters157
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.15, −0.21

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2A···O1i0.841.862.6529 (14)156.4
Symmetry code: (i) −x+1, y+1/2, −z+1/2.
 

Acknowledgements

Financial support of this work by the inter­nal grant of TBU in Zlín No. IGA/7/FT/10/D, funded from the resources of specific university research, is gratefully acknowledged.

References

First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
 First citationKafka, S., Klásek, A., Polis, J. & Košmrlj, J. (2002). Heterocycles, 57, 1659–1682.  CAS Google Scholar
 First citationKlásek, A., Kafka, S., Polis, J. & Košmrlj, J. (1998). Heterocycles, 48, 2309–2326.  Google Scholar
 First citationMacrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationOxford Diffraction (2009). CrysAlis CCD and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationStadlbauer, W. & Kappe, T. (1985). Monatsch. Chem. 116, 1005–1015.  CrossRef CAS Google Scholar

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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3196
https://doi.org/10.1107/S160053681004643X
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