Ethyl 2-(quinolin-8-yl­oxy)acetate monohydrate

Kumar, M.; Mallikarjunaswamy, C.; Sridhar, M.A.; Bhadregowda, D.G.; Kapoor, K.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536813008106

organic compounds

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Volume 69| Part 4| April 2013| Page o623

doi:10.1107/S1600536813008106

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Ethyl 2-(quinolin-8-yloxy)acetate monohydrate

Mohan Kumar,^a C. Mallikarjunaswamy,^b M. A. Sridhar,^a ^* D. G. Bhadregowda,^b Kamini Kapoor,^c Vivek K. Gupta ^c and Rajni Kant ^c

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, ^bDepartment of Chemistry, Yuvarajas College, University of Mysore, Mysore 570005, India, and ^cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
^*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 16 March 2013; accepted 24 March 2013; online 28 March 2013)

In the title compound, C₁₃H₁₃NO₃·H₂O, the dihedral angle between the ethyl ester group [C—C—O—C(=O); maximum deviation = 0.003 (2) Å] and the quinoline ring system is 7.94 (12)°. The water solvent molecule is linked to the title molecule via O—H⋯O and O—H⋯N hydrogen bonds. In the crystal, molecules are linked by C—H⋯O hydrogen bonds, forming chains propagating along [100].

Related literature

For related structures see: Sarveswari et al. (2010 ); Ukrainets et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₃H₁₃NO₃·H₂O
M_r = 249.26
Monoclinic, P 2₁ /n
a = 6.9562 (4) Å
b = 17.5050 (9) Å
c = 10.5304 (6) Å
β = 100.124 (5)°
V = 1262.30 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.715, T_max = 1.000
9808 measured reflections
2478 independent reflections
1448 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.123
S = 1.02
2478 reflections
172 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W⋯O5	0.85 (3)	2.06 (3)	2.907 (3)	172
O1W—H2W⋯N16	0.92 (3)	1.96 (3)	2.875 (3)	174
C6—H6A⋯O1Wⁱ	0.97	2.43	3.388 (3)	170
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813008106/su2575sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813008106/su2575Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813008106/su2575Isup3.cml

checkCIF report

Comment top

In the title molecule, Fig. 1, the bond lengths (Allen et al., 1987) and angles have normal values and are comparable with those reported for similar structures (Sarveswari et al., 2010; Ukrainets et al., 2009). The dihedral angle between the ethyl ester group (C1/C2/O3/C4/O5) and the quinoline (C8—C15/N16/C17) ring system is 7.94 (12)°. The solvent water molecule is linked to the title molecule via O-H···O and O-H···N hydrogen bonds (Fig. 1 and Table 1).

In the crystal, molecules are linked by C—H···O hydrogen bonds (Table 1) forming chains propagating along the a axis direction (Fig. 2).

Related literature top

For related structures see: Sarveswari et al. (2010); Ukrainets et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

A mixture of 8-hydroxy quinoline(0.01 mol) and ethyl chloroacetate (0.015 mol) in the presence of dry acetone (50 ml) and anhydrous potassium carbonate (0.015 mol) was refluxed for 8 h. The residual mass was triturated with cold water to remove potassium carbonate and extracted with ether (30 ml). The ether layer was washed with 10% sodium hydroxide solution (350 ml) followed by water (330 ml) and then dried over anhydrous sodium sulfate and evaporated to dryness. The compound was purified by successive recrystallizations from ethanol yielding colourless block-like crystals (Yield 90%, m.p. 350–352 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 40% probability level. The O-H···O and O-H···N hydrogen bonds are shown as dashed lines (see Table for details).
	Fig. 2. The crystal packing of the title compound view along the a axis, showing the O—H···O, O—H···N and C-H···O hydrogen bonds as dashed lines (see Table 1 for details).

Ethyl 2-(quinolin-8-yloxy)acetate monohydrate top

Crystal data top

C₁₃H₁₃NO₃·H₂O	F(000) = 528
M_r = 249.26	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3127 reflections
a = 6.9562 (4) Å	θ = 3.5–29.0°
b = 17.5050 (9) Å	µ = 0.10 mm⁻¹
c = 10.5304 (6) Å	T = 293 K
β = 100.124 (5)°	Block, colourless
V = 1262.30 (12) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2478 independent reflections
Radiation source: fine-focus sealed tube	1448 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scans	h = −8→8
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
T_min = 0.715, T_max = 1.000	l = −11→12
9808 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0382P)² + 0.1537P] where P = (F_o² + 2F_c²)/3
2478 reflections	(Δ/σ)_max = 0.001
172 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₃H₁₃NO₃·H₂O	V = 1262.30 (12) Å³
M_r = 249.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9562 (4) Å	µ = 0.10 mm⁻¹
b = 17.5050 (9) Å	T = 293 K
c = 10.5304 (6) Å	0.3 × 0.2 × 0.2 mm
β = 100.124 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	2478 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	1448 reflections with I > 2σ(I)
T_min = 0.715, T_max = 1.000	R_int = 0.051
9808 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.14 e Å⁻³
2478 reflections	Δρ_min = −0.19 e Å⁻³
172 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 > 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

	x	y	z	U_iso*/U_eq
C1	0.1064 (4)	−0.11734 (16)	−0.0152 (2)	0.0746 (9)
H1A	0.1136	−0.1608	0.0410	0.112*
H1B	0.1291	−0.1334	−0.0985	0.112*
H1C	−0.0208	−0.0946	−0.0237	0.112*
C2	0.2574 (4)	−0.06026 (15)	0.0399 (2)	0.0605 (7)
H2A	0.3868	−0.0825	0.0481	0.073*
H2B	0.2511	−0.0160	−0.0160	0.073*
O3	0.2179 (2)	−0.03807 (9)	0.16644 (14)	0.0527 (5)
C4	0.3381 (3)	0.01324 (13)	0.2305 (2)	0.0431 (6)
O5	0.4722 (3)	0.04156 (11)	0.19103 (16)	0.0671 (6)
C6	0.2763 (3)	0.03087 (12)	0.35690 (19)	0.0407 (6)
H6A	0.1472	0.0537	0.3421	0.049*
H6B	0.2717	−0.0157	0.4062	0.049*
O7	0.4143 (2)	0.08241 (8)	0.42563 (13)	0.0440 (4)
C8	0.3737 (3)	0.11137 (12)	0.5390 (2)	0.0374 (5)
C9	0.2176 (3)	0.09077 (14)	0.5928 (2)	0.0501 (6)
H9	0.1299	0.0544	0.5529	0.060*
C10	0.1893 (4)	0.12463 (16)	0.7087 (2)	0.0628 (7)
H10	0.0824	0.1100	0.7451	0.075*
C11	0.3136 (4)	0.17809 (16)	0.7690 (2)	0.0630 (8)
H11	0.2902	0.2006	0.8449	0.076*
C12	0.4787 (4)	0.19961 (13)	0.7166 (2)	0.0471 (6)
C13	0.6180 (4)	0.25321 (14)	0.7755 (2)	0.0595 (7)
H13	0.6003	0.2777	0.8510	0.071*
C14	0.7760 (4)	0.26897 (14)	0.7230 (2)	0.0582 (7)
H14	0.8698	0.3035	0.7620	0.070*
C15	0.7960 (4)	0.23238 (13)	0.6085 (2)	0.0538 (7)
H15	0.9056	0.2441	0.5728	0.065*
N16	0.6718 (3)	0.18260 (11)	0.54715 (17)	0.0466 (5)
C17	0.5122 (3)	0.16581 (12)	0.6004 (2)	0.0383 (5)
O1W	0.8236 (3)	0.10488 (13)	0.3454 (2)	0.0723 (6)
H2W	0.770 (5)	0.1318 (18)	0.406 (3)	0.123 (14)*
H1W	0.728 (5)	0.0844 (18)	0.295 (3)	0.109 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.099 (2)	0.0701 (19)	0.0512 (16)	−0.0165 (17)	0.0026 (16)	−0.0184 (14)
C2	0.0763 (19)	0.0683 (18)	0.0396 (14)	−0.0050 (15)	0.0171 (13)	−0.0153 (13)
O3	0.0602 (11)	0.0590 (11)	0.0403 (9)	−0.0135 (9)	0.0124 (8)	−0.0143 (8)
C4	0.0463 (14)	0.0449 (14)	0.0378 (13)	0.0001 (12)	0.0067 (11)	−0.0053 (11)
O5	0.0646 (12)	0.0882 (14)	0.0534 (11)	−0.0269 (11)	0.0243 (9)	−0.0198 (10)
C6	0.0409 (13)	0.0417 (13)	0.0394 (12)	−0.0017 (10)	0.0065 (10)	−0.0068 (10)
O7	0.0484 (9)	0.0490 (10)	0.0359 (8)	−0.0061 (8)	0.0110 (7)	−0.0102 (7)
C8	0.0442 (13)	0.0353 (12)	0.0327 (12)	0.0049 (10)	0.0067 (10)	−0.0018 (10)
C9	0.0499 (15)	0.0598 (17)	0.0424 (14)	−0.0055 (13)	0.0129 (12)	−0.0047 (12)
C10	0.0585 (17)	0.083 (2)	0.0517 (16)	−0.0014 (15)	0.0234 (13)	−0.0074 (15)
C11	0.0686 (18)	0.079 (2)	0.0443 (15)	0.0070 (16)	0.0184 (14)	−0.0182 (14)
C12	0.0577 (15)	0.0410 (14)	0.0413 (13)	0.0083 (12)	0.0054 (12)	−0.0041 (11)
C13	0.0715 (19)	0.0504 (16)	0.0531 (15)	0.0103 (14)	0.0015 (14)	−0.0194 (13)
C14	0.0637 (18)	0.0478 (16)	0.0590 (17)	−0.0028 (13)	−0.0003 (14)	−0.0094 (13)
C15	0.0588 (16)	0.0491 (15)	0.0524 (15)	−0.0068 (13)	0.0073 (13)	0.0025 (13)
N16	0.0512 (12)	0.0438 (12)	0.0446 (11)	−0.0055 (10)	0.0079 (10)	−0.0040 (9)
C17	0.0450 (13)	0.0358 (13)	0.0335 (12)	0.0054 (11)	0.0051 (10)	0.0010 (10)
O1W	0.0525 (12)	0.0896 (16)	0.0786 (15)	−0.0139 (11)	0.0217 (11)	−0.0260 (13)

Geometric parameters (Å, º) top

C1—C2	1.492 (3)	C9—H9	0.9300
C1—H1A	0.9600	C10—C11	1.354 (3)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.410 (3)
C2—O3	1.460 (3)	C11—H11	0.9300
C2—H2A	0.9700	C12—C13	1.412 (3)
C2—H2B	0.9700	C12—C17	1.414 (3)
O3—C4	1.328 (2)	C13—C14	1.344 (3)
C4—O5	1.194 (3)	C13—H13	0.9300
C4—C6	1.501 (3)	C14—C15	1.393 (3)
C6—O7	1.420 (2)	C14—H14	0.9300
C6—H6A	0.9700	C15—N16	1.314 (3)
C6—H6B	0.9700	C15—H15	0.9300
O7—C8	1.371 (2)	N16—C17	1.361 (3)
C8—C9	1.359 (3)	O1W—H2W	0.93 (4)
C8—C17	1.427 (3)	O1W—H1W	0.85 (4)
C9—C10	1.401 (3)

C2—C1—H1A	109.5	C8—C9—C10	119.7 (2)
C2—C1—H1B	109.5	C8—C9—H9	120.1
H1A—C1—H1B	109.5	C10—C9—H9	120.1
C2—C1—H1C	109.5	C11—C10—C9	121.7 (2)
H1A—C1—H1C	109.5	C11—C10—H10	119.2
H1B—C1—H1C	109.5	C9—C10—H10	119.2
O3—C2—C1	107.5 (2)	C10—C11—C12	119.9 (2)
O3—C2—H2A	110.2	C10—C11—H11	120.1
C1—C2—H2A	110.2	C12—C11—H11	120.1
O3—C2—H2B	110.2	C11—C12—C13	123.3 (2)
C1—C2—H2B	110.2	C11—C12—C17	119.8 (2)
H2A—C2—H2B	108.5	C13—C12—C17	117.0 (2)
C4—O3—C2	116.17 (19)	C14—C13—C12	120.2 (2)
O5—C4—O3	124.4 (2)	C14—C13—H13	119.9
O5—C4—C6	125.9 (2)	C12—C13—H13	119.9
O3—C4—C6	109.7 (2)	C13—C14—C15	118.4 (2)
O7—C6—C4	108.00 (18)	C13—C14—H14	120.8
O7—C6—H6A	110.1	C15—C14—H14	120.8
C4—C6—H6A	110.1	N16—C15—C14	125.0 (3)
O7—C6—H6B	110.1	N16—C15—H15	117.5
C4—C6—H6B	110.1	C14—C15—H15	117.5
H6A—C6—H6B	108.4	C15—N16—C17	117.0 (2)
C8—O7—C6	117.01 (17)	N16—C17—C12	122.4 (2)
C9—C8—O7	124.6 (2)	N16—C17—C8	119.47 (19)
C9—C8—C17	120.9 (2)	C12—C17—C8	118.1 (2)
O7—C8—C17	114.56 (19)	H2W—O1W—H1W	107 (3)

C1—C2—O3—C4	−179.6 (2)	C17—C12—C13—C14	−1.4 (3)
C2—O3—C4—O5	0.3 (3)	C12—C13—C14—C15	1.2 (4)
C2—O3—C4—C6	179.04 (19)	C13—C14—C15—N16	−0.4 (4)
O5—C4—C6—O7	−4.6 (3)	C14—C15—N16—C17	−0.1 (3)
O3—C4—C6—O7	176.69 (16)	C15—N16—C17—C12	−0.1 (3)
C4—C6—O7—C8	173.95 (17)	C15—N16—C17—C8	−179.14 (19)
C6—O7—C8—C9	4.0 (3)	C11—C12—C17—N16	−178.0 (2)
C6—O7—C8—C17	−176.90 (17)	C13—C12—C17—N16	0.9 (3)
O7—C8—C9—C10	−179.4 (2)	C11—C12—C17—C8	1.0 (3)
C17—C8—C9—C10	1.5 (3)	C13—C12—C17—C8	179.91 (19)
C8—C9—C10—C11	0.3 (4)	C9—C8—C17—N16	177.0 (2)
C9—C10—C11—C12	−1.4 (4)	O7—C8—C17—N16	−2.2 (3)
C10—C11—C12—C13	−178.1 (2)	C9—C8—C17—C12	−2.1 (3)
C10—C11—C12—C17	0.7 (4)	O7—C8—C17—C12	178.72 (18)
C11—C12—C13—C14	177.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O5	0.85 (3)	2.06 (3)	2.907 (3)	172
O1W—H2W···N16	0.92 (3)	1.96 (3)	2.875 (3)	174
C6—H6A···O1Wⁱ	0.97	2.43	3.388 (3)	170

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃NO₃·H₂O
M_r	249.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.9562 (4), 17.5050 (9), 10.5304 (6)
β (°)	100.124 (5)
V (Å³)	1262.30 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.715, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	9808, 2478, 1448
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.123, 1.02
No. of reflections	2478
No. of parameters	172
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.19

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···O5	0.85 (3)	2.06 (3)	2.907 (3)	172
O1W—H2W···N16	0.92 (3)	1.96 (3)	2.875 (3)	174
C6—H6A···O1Wⁱ	0.97	2.43	3.388 (3)	170

Symmetry code: (i) x−1, y, z.

Acknowledgements

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola, for his research work. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

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