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

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].

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.053
• wR factor = 0.123
• Data-to-parameter ratio = 14.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     13.776
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      2.346
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          5

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF          ?
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported   _diffrn_ambient_temperature        293 K

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   4 ALERT level G = General information/check it is not something unexpected

   2 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
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: As the reported work is a part of collaboration between three Universities. Hence the number of authors are greater than 5. Synthesis has been carried out by Mohan Kumar, C. Mallikarjunaswamy, M. A. Sridhar and D.G. Bhadregowda while Kamini Kapoor, Vivek Gupta and Rajnikant are responsible for the single crystal growth, X-ray data collection, refinement of the structure, structure completion in the form of paper and for bearing the financial load for the publication.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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S1. Comment

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

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

S2. Experimental

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).

S3. Refinement

The water molecule H atoms were located in a difference Fourier map and freely refined. The C-bound H atoms were positioned geometrically and treated as riding atoms: C—H distances of 0.93–0.97 Å with U_iso(H) = 1.5U_eq(methyl C) and = 1.2U_eq(C) for other H atoms.

Computing details

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

	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

Crystal data

C13H13NO3·H2O	F(000) = 528
Mr = 249.26	Dx = 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) Å^3	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection

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

Refinement

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

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.

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O1W^i	0.97	2.43	3.388 (3)	170

Symmetry code: (i) x−1, y, z.