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In the title compound, C11H16O5, inter­molecular O—H...O hydrogen bonds are observed which help to establish the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807043838/hg2292sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807043838/hg2292Isup2.hkl
Contains datablock I

CCDC reference: 664200

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.045
  • wR factor = 0.126
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 400 Deg. PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
Alert level G PLAT793_ALERT_1_G Check the Absolute Configuration of C4 = ... R PLAT793_ALERT_1_G Check the Absolute Configuration of C7 = ... R PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 12
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 5 Informative message, check

Comment top

The title compound (I) is obtained as a by-product in the synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine. We report here the crystal structure of the title compound (I) (Fig. 1). In the crystal, O—H···O hydrogen bonds link the molecules into chains. Table 1. The structure of the related cyclohexyl compound has been reported previously by Lalancette et al. (1995).

Related literature top

For the preparation of the title compound, see Westman & Kober (1964); for a related compound, see Lalancette et al. (1995).

Experimental top

The title compound was prepared according to the method of Westman & Kober (1964). Methyl 3-(2-cyanoethyl)-1-(3-methoxy-3-oxopropyl) -2-oxocyclopentanecarboxylate (14.06 g, 0.05 mol) was refluxed for 3 h, with 27 ml of concentrated hydrochloric acid. At the end of this period, the solution was evaporated to dryness in vacuo (steam bath), and the solid residue was triturated with 50 ml e thanol. Removal of ammonium chloride by filtration and evaporation of the ethanol yielded 80% of 3,3'-(2-oxocyclopentane-1,3-diyl)dipropanoic acid, after two recrystallizations from dioxane-hexane. Crystals of (I) were obtained by slow evaporation of a solution of ethyl acetate (m.p. 394–395 K).

Refinement top

All H atoms were positioned geometrically (C—H = 0.97–0.98 Å), and refined as riding with Uiso(H) = 1.2Ueq (carrier) or 1.5eq (methyl groups).

Structure description top

The title compound (I) is obtained as a by-product in the synthesis of 6,7-dihydro-5H-cyclopenta[b]pyridine. We report here the crystal structure of the title compound (I) (Fig. 1). In the crystal, O—H···O hydrogen bonds link the molecules into chains. Table 1. The structure of the related cyclohexyl compound has been reported previously by Lalancette et al. (1995).

For the preparation of the title compound, see Westman & Kober (1964); for a related compound, see Lalancette et al. (1995).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top
[Figure 1] Fig. 1. A view of the molecular of (I). Displacement ellopsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
3,3'-(2-Oxocyclopentane-1,3-diyl)dipropanoic acid top
Crystal data top
C11H16O5Z = 2
Mr = 228.24F(000) = 244
Triclinic, P1Dx = 1.295 Mg m3
Hall symbol: -P 1Melting point: 394-395 K K
a = 6.7644 (17) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.386 (2) ÅCell parameters from 1257 reflections
c = 9.855 (3) Åθ = 2.9–25.7°
α = 95.510 (4)°µ = 0.10 mm1
β = 101.915 (4)°T = 294 K
γ = 104.563 (4)°Block, colorless
V = 585.3 (3) Å30.26 × 0.22 × 0.10 mm
Data collection top
Bruker SMART CCD area detector
diffractometer
2035 independent reflections
Radiation source: fine-focus sealed tube1452 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.015
φ and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
h = 78
Tmin = 0.974, Tmax = 0.990k = 118
3011 measured reflectionsl = 1111
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.1943P]
where P = (Fo2 + 2Fc2)/3
2035 reflections(Δ/σ)max < 0.001
147 parametersΔρmax = 0.22 e Å3
12 restraintsΔρmin = 0.19 e Å3
Crystal data top
C11H16O5γ = 104.563 (4)°
Mr = 228.24V = 585.3 (3) Å3
Triclinic, P1Z = 2
a = 6.7644 (17) ÅMo Kα radiation
b = 9.386 (2) ŵ = 0.10 mm1
c = 9.855 (3) ÅT = 294 K
α = 95.510 (4)°0.26 × 0.22 × 0.10 mm
β = 101.915 (4)°
Data collection top
Bruker SMART CCD area detector
diffractometer
2035 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
1452 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.990Rint = 0.015
3011 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04512 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.03Δρmax = 0.22 e Å3
2035 reflectionsΔρmin = 0.19 e Å3
147 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
xyzUiso*/Ueq
O10.9983 (4)0.8289 (2)0.4371 (2)0.0967 (7)
H11.04060.88530.49000.145*
O20.8445 (3)1.0024 (2)0.3900 (2)0.0815 (6)
O30.2993 (2)0.8393 (2)0.05699 (17)0.0666 (5)
O40.0373 (2)0.55634 (18)0.34961 (16)0.0602 (5)
O50.2803 (2)0.5835 (2)0.54718 (16)0.0687 (5)
H50.17790.54220.57530.103*
C10.8831 (4)0.8854 (3)0.3694 (2)0.0555 (6)
C20.8024 (4)0.7925 (3)0.2688 (2)0.0574 (6)
H2A0.92150.78190.20050.069*
H2B0.72450.69390.31950.069*
C30.6618 (3)0.8517 (3)0.1907 (2)0.0506 (5)
H3A0.73270.95400.14700.061*
H3B0.53340.85100.25670.061*
C40.6072 (3)0.7591 (2)0.0791 (2)0.0483 (5)
H40.54450.65580.12610.058*
C50.7912 (4)0.7589 (3)0.0396 (3)0.0666 (7)
H5A0.88910.85770.06830.080*
H5B0.86570.68990.01110.080*
C60.6900 (4)0.7096 (3)0.1585 (3)0.0632 (7)
H6A0.63530.60190.14490.076*
H6B0.79100.74250.24850.076*
C70.5122 (3)0.7837 (2)0.1506 (2)0.0477 (5)
H70.57170.88410.20500.057*
C80.4500 (3)0.7998 (2)0.0036 (2)0.0460 (5)
C90.3272 (3)0.7044 (3)0.2067 (2)0.0519 (6)
H9A0.22190.75880.19410.062*
H9B0.26380.60540.15260.062*
C100.3917 (3)0.6911 (3)0.3610 (2)0.0556 (6)
H10A0.50540.64440.37410.067*
H10B0.44530.79050.41520.067*
C110.2184 (3)0.6037 (2)0.4173 (2)0.0481 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.1374 (19)0.1006 (16)0.1023 (16)0.0674 (14)0.0866 (15)0.0393 (12)
O20.1068 (15)0.0789 (13)0.0915 (14)0.0421 (12)0.0680 (12)0.0294 (11)
O30.0482 (9)0.1018 (14)0.0617 (10)0.0314 (9)0.0175 (8)0.0319 (10)
O40.0482 (9)0.0817 (12)0.0521 (9)0.0130 (8)0.0148 (7)0.0254 (8)
O50.0500 (9)0.1064 (14)0.0519 (10)0.0147 (9)0.0160 (8)0.0334 (9)
C10.0558 (14)0.0672 (17)0.0470 (13)0.0191 (12)0.0204 (11)0.0027 (12)
C20.0601 (14)0.0632 (15)0.0541 (14)0.0203 (12)0.0212 (11)0.0091 (12)
C30.0497 (12)0.0577 (14)0.0473 (12)0.0143 (10)0.0182 (10)0.0098 (11)
C40.0425 (11)0.0489 (13)0.0541 (13)0.0099 (9)0.0152 (10)0.0105 (10)
C50.0489 (13)0.096 (2)0.0675 (16)0.0296 (13)0.0224 (12)0.0326 (15)
C60.0507 (13)0.0838 (18)0.0655 (15)0.0246 (12)0.0194 (11)0.0334 (14)
C70.0441 (12)0.0530 (13)0.0471 (12)0.0102 (9)0.0136 (9)0.0161 (10)
C80.0377 (11)0.0501 (13)0.0497 (12)0.0074 (9)0.0125 (9)0.0144 (10)
C90.0442 (12)0.0636 (15)0.0506 (13)0.0122 (10)0.0155 (10)0.0206 (11)
C100.0490 (12)0.0684 (16)0.0533 (13)0.0152 (11)0.0171 (10)0.0208 (12)
C110.0484 (13)0.0565 (14)0.0472 (12)0.0212 (10)0.0168 (10)0.0164 (11)
Geometric parameters (Å, º) top
O1—C11.299 (3)C4—H40.9800
O1—H10.8200C5—C61.527 (3)
O2—C11.217 (3)C5—H5A0.9700
O3—C81.207 (2)C5—H5B0.9700
O4—C111.215 (3)C6—C71.526 (3)
O5—C111.309 (2)C6—H6A0.9700
O5—H50.8200C6—H6B0.9700
C1—C21.480 (3)C7—C81.524 (3)
C2—C31.514 (3)C7—C91.524 (3)
C2—H2A0.9700C7—H70.9800
C2—H2B0.9700C9—C101.519 (3)
C3—C41.514 (3)C9—H9A0.9700
C3—H3A0.9700C9—H9B0.9700
C3—H3B0.9700C10—C111.493 (3)
C4—C81.519 (3)C10—H10A0.9700
C4—C51.523 (3)C10—H10B0.9700
C1—O1—H1109.5C7—C6—H6A110.8
C11—O5—H5109.5C5—C6—H6A110.8
O2—C1—O1122.3 (2)C7—C6—H6B110.8
O2—C1—C2124.2 (2)C5—C6—H6B110.8
O1—C1—C2113.5 (2)H6A—C6—H6B108.9
C1—C2—C3115.3 (2)C8—C7—C9113.28 (17)
C1—C2—H2A108.4C8—C7—C6104.12 (17)
C3—C2—H2A108.4C9—C7—C6115.81 (18)
C1—C2—H2B108.4C8—C7—H7107.8
C3—C2—H2B108.4C9—C7—H7107.8
H2A—C2—H2B107.5C6—C7—H7107.8
C4—C3—C2111.47 (19)O3—C8—C4125.5 (2)
C4—C3—H3A109.3O3—C8—C7125.13 (19)
C2—C3—H3A109.3C4—C8—C7109.38 (17)
C4—C3—H3B109.3C10—C9—C7112.54 (18)
C2—C3—H3B109.3C10—C9—H9A109.1
H3A—C3—H3B108.0C7—C9—H9A109.1
C3—C4—C8115.83 (18)C10—C9—H9B109.1
C3—C4—C5115.83 (18)C7—C9—H9B109.1
C8—C4—C5103.80 (18)H9A—C9—H9B107.8
C3—C4—H4106.9C11—C10—C9114.30 (19)
C8—C4—H4106.9C11—C10—H10A108.7
C5—C4—H4106.9C9—C10—H10A108.7
C4—C5—C6104.44 (18)C11—C10—H10B108.7
C4—C5—H5A110.9C9—C10—H10B108.7
C6—C5—H5A110.9H10A—C10—H10B107.6
C4—C5—H5B110.9O4—C11—O5123.20 (19)
C6—C5—H5B110.9O4—C11—C10123.33 (19)
H5A—C5—H5B108.9O5—C11—C10113.47 (19)
C7—C6—C5104.61 (17)
O2—C1—C2—C30.7 (4)C3—C4—C8—C7142.55 (19)
O1—C1—C2—C3178.2 (2)C5—C4—C8—C714.4 (2)
C1—C2—C3—C4173.6 (2)C9—C7—C8—O345.1 (3)
C2—C3—C4—C8174.42 (19)C6—C7—C8—O3171.7 (2)
C2—C3—C4—C563.7 (3)C9—C7—C8—C4135.13 (19)
C3—C4—C5—C6159.9 (2)C6—C7—C8—C48.5 (2)
C8—C4—C5—C631.8 (2)C8—C7—C9—C10179.26 (19)
C4—C5—C6—C737.8 (3)C6—C7—C9—C1060.5 (3)
C5—C6—C7—C828.1 (2)C7—C9—C10—C11175.48 (19)
C5—C6—C7—C9153.2 (2)C9—C10—C11—O45.3 (3)
C3—C4—C8—O337.2 (3)C9—C10—C11—O5175.0 (2)
C5—C4—C8—O3165.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.822.639 (2)173
O5—H5···O4ii0.821.852.667 (2)175
Symmetry codes: (i) x+2, y+2, z1; (ii) x, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC11H16O5
Mr228.24
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)6.7644 (17), 9.386 (2), 9.855 (3)
α, β, γ (°)95.510 (4), 101.915 (4), 104.563 (4)
V3)585.3 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.26 × 0.22 × 0.10
Data collection
DiffractometerBruker SMART CCD area detector
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.974, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
3011, 2035, 1452
Rint0.015
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.126, 1.03
No. of reflections2035
No. of parameters147
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.19

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.822.639 (2)173.3
O5—H5···O4ii0.821.852.667 (2)175.0
Symmetry codes: (i) x+2, y+2, z1; (ii) x, y+1, z+1.
 

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