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ISSN: 2056-9890

Butane-1,4-diyl bis­­(pyridine-4-carboxyl­ate)

aCentre for Bioinformatics, Pondicherry University, Puducherry 605 014, India, and bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
*Correspondence e-mail: krishstrucbio@gmail.com

(Received 15 June 2011; accepted 16 June 2011; online 25 June 2011)

The mol­ecule of the title compound, C16H16N2O4, lies about an inversion centre; the butane chain adopts an extended zigzag conformation. The dihedral angle between the pyridine ring and the adjacent COO group is 3.52 (s14)°.

Related literature

For a related structure, see: Brito et al. (2010[Brito, I., Vallejos, J., Bolte, M., López-Rodríguez, M. & Cárdenas, A. (2010). Acta Cryst. E66, o1015.]).

[Scheme 1]

Experimental

Crystal data
  • C16H16N2O4

  • Mr = 300.31

  • Monoclinic, P 21 /c

  • a = 7.8519 (5) Å

  • b = 10.5284 (6) Å

  • c = 8.9121 (4) Å

  • β = 91.770 (5)°

  • V = 736.39 (7) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 293 K

  • 0.35 × 0.13 × 0.04 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.840, Tmax = 1.000

  • 2431 measured reflections

  • 1303 independent reflections

  • 754 reflections with I > 2σ(I)

  • Rint = 0.018

Refinement
  • R[F2 > 2σ(F2)] = 0.039

  • wR(F2) = 0.102

  • S = 0.87

  • 1303 reflections

  • 100 parameters

  • H-atom parameters constrained

  • Δρmax = 0.18 e Å−3

  • Δρmin = −0.13 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. 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 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.

Supporting information


Comment top

Pyridine containing compounds are the new class of anti-HIV molecules, which particularly inhibit RNA dependent DNA polymerase or reverse transcriptase, and hence it acts as non-nucleoside reverse transcriptase inhibitors. They also posses potent anti-bacterial activity. Pyridine containing ruthenium complexes exhibit cytotoxic, anti-cancer, anti-tumor or anti-metastatic activity. Considering the biological importances of the pyridine and its derivatives, a single-crystal of the title compound was prepared for X-ray diffraction studies. The molecular structure of title compound is shown in Fig. 1. The bond distances of pyridyl group in title compound is comparable to those observed in related structure namely propane-1,3-diyl bis(pyridine-4-carboxylate) (Brito et al., 2010). The pyridyl group (N1/C4/C3/C2/C6/C5) adopts a planar conformation (r.m.s. deviation = 0.0019 Å). Cremer & Pople puckering analysis fails, because of its weighted average absolute torsion angle is 0.4°, which is less than 5.0°. The 1,4-butanediyl ester group occupies an equatorial position, which adopt an extended zigzag conformation. Intermolecular π-π stacking interactions is normally found in aromatic compounds. However, in the title compound, the minimal distance between ring centroids is 4.357 (1) Å. Hence, intermolecular π-π stacking interactions are not present in the title compound. The classical hydrogen bonds are not observed. The packing diagram of title compound is shown in Fig. 2.

Related literature top

For a related structure, see: Brito et al. (2010).

Experimental top

Isonicotinoyl chloride hydrochloride (639 mg, 3.5 mmol) was taken in a 50 ml round bottom schlenk flask and fitted with a reflux condenser. The system was evacuated and purged with nitrogen. To this, dry dichloromethane 25 ml, 1,4-Butanediol (0.15 ml, 1.7 mmol) and 1 ml of triethylamine were added. The reaction mixture was heated at 40 °C for 5 h. After, the mixture was washed with saturated aqueous sodium bicarbonate solution (20 ml), the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated using vacuum and the white product was purified by recrystallization with dichloromethane (Yield: 87%, Melting Point: 140 °C). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in dichloromethane at room temperature. Spectroscopic data of the title compound: IR (KBr): 3046 (w), 1728 (s), 1560 (w), 1476 (w), 1286 (s), 1127 (s), 755 (m), cm-1. 1H NMR (400 MHz, CDCl3): δ 8.77 (d, 4H), 7.83 (d, 4H), 4.43–4.42 (m, 4H), 1.97–1.94 (m, 4H). 13C NMR (100 MHz, CDCl3): δ 165.2, 150.7, 137.4, 122.9, 65.2, 25.3.

Refinement top

The non-hydrogen atoms were refined anisotropically whereas hydrogen atoms were refined isotropically. The hydrogen atoms were placed in calculated positions (C–H = 0.93–0.97 Å) and included in the refinement in riding-model approximation with Uiso(H) = 1.2Ueq(C).

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 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of title compound, showing displacement ellipsoids drawn at the 50% probability level.
[Figure 2] Fig. 2. Packing diagram of title compound.
Butane-1,4-diyl bis(pyridine-4-carboxylate) top
Crystal data top
C16H16N2O4F(000) = 316
Mr = 300.31Dx = 1.354 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 852 reflections
a = 7.8519 (5) Åθ = 2.6–28.6°
b = 10.5284 (6) ŵ = 0.10 mm1
c = 8.9121 (4) ÅT = 293 K
β = 91.770 (5)°Plate, colorless
V = 736.39 (7) Å30.35 × 0.13 × 0.04 mm
Z = 2
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
1303 independent reflections
Radiation source: fine-focus sealed tube754 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.018
Detector resolution: 15.9821 pixels mm-1θmax = 25.0°, θmin = 2.6°
ω scansh = 97
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
k = 127
Tmin = 0.840, Tmax = 1.000l = 610
2431 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H-atom parameters constrained
S = 0.87 w = 1/[σ2(Fo2) + (0.0561P)2]
where P = (Fo2 + 2Fc2)/3
1303 reflections(Δ/σ)max = 0.001
100 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C16H16N2O4V = 736.39 (7) Å3
Mr = 300.31Z = 2
Monoclinic, P21/cMo Kα radiation
a = 7.8519 (5) ŵ = 0.10 mm1
b = 10.5284 (6) ÅT = 293 K
c = 8.9121 (4) Å0.35 × 0.13 × 0.04 mm
β = 91.770 (5)°
Data collection top
Oxford Diffraction Xcalibur Eos
diffractometer
1303 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
754 reflections with I > 2σ(I)
Tmin = 0.840, Tmax = 1.000Rint = 0.018
2431 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0390 restraints
wR(F2) = 0.102H-atom parameters constrained
S = 0.87Δρmax = 0.18 e Å3
1303 reflectionsΔρmin = 0.13 e Å3
100 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
O10.33092 (14)0.50761 (11)0.18817 (12)0.0510 (4)
C20.21740 (19)0.51211 (16)0.05823 (17)0.0389 (4)
C10.2787 (2)0.58307 (18)0.0775 (2)0.0466 (5)
O20.2806 (2)0.69674 (13)0.08561 (15)0.0789 (5)
C30.1504 (2)0.57907 (18)0.17878 (19)0.0504 (5)
H30.14380.66720.17530.060*
C60.2231 (2)0.38214 (18)0.06986 (19)0.0529 (5)
H60.26630.33270.00900.063*
N10.0981 (2)0.39039 (17)0.31796 (17)0.0607 (5)
C40.0936 (2)0.5144 (2)0.3041 (2)0.0546 (6)
H40.04910.56140.38440.065*
C70.3923 (2)0.57013 (18)0.32514 (19)0.0539 (6)
H7A0.30010.61620.37050.065*
H7B0.48190.63000.30260.065*
C80.4589 (2)0.47077 (18)0.42959 (18)0.0465 (5)
H8A0.54240.41950.37920.056*
H8B0.36630.41560.45770.056*
C50.1632 (3)0.3269 (2)0.2011 (2)0.0645 (6)
H50.16880.23890.20840.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0716 (8)0.0474 (8)0.0329 (7)0.0001 (6)0.0175 (6)0.0006 (6)
C20.0430 (10)0.0424 (10)0.0310 (9)0.0030 (8)0.0023 (8)0.0006 (9)
C10.0597 (12)0.0440 (11)0.0356 (10)0.0006 (10)0.0063 (9)0.0026 (10)
O20.1401 (14)0.0422 (9)0.0522 (9)0.0013 (9)0.0322 (8)0.0016 (7)
C30.0659 (13)0.0436 (11)0.0410 (11)0.0005 (10)0.0108 (10)0.0029 (9)
C60.0726 (13)0.0466 (12)0.0386 (11)0.0012 (10)0.0110 (10)0.0022 (10)
N10.0755 (12)0.0600 (12)0.0454 (10)0.0034 (9)0.0162 (9)0.0042 (9)
C40.0683 (14)0.0590 (13)0.0353 (10)0.0028 (11)0.0156 (9)0.0027 (10)
C70.0710 (13)0.0542 (13)0.0353 (10)0.0022 (10)0.0185 (10)0.0059 (9)
C80.0540 (11)0.0516 (11)0.0331 (9)0.0001 (9)0.0111 (8)0.0010 (9)
C50.0927 (16)0.0447 (12)0.0553 (13)0.0060 (11)0.0134 (12)0.0084 (11)
Geometric parameters (Å, º) top
O1—C11.322 (2)N1—C41.312 (2)
O1—C71.4558 (19)N1—C51.326 (2)
C2—C61.373 (2)C4—H40.9300
C2—C31.376 (2)C7—C81.485 (2)
C2—C11.489 (2)C7—H7A0.9700
C1—O21.199 (2)C7—H7B0.9700
C3—C41.371 (2)C8—C8i1.523 (3)
C3—H30.9300C8—H8A0.9700
C6—C51.376 (2)C8—H8B0.9700
C6—H60.9300C5—H50.9300
C1—O1—C7116.16 (14)C3—C4—H4117.9
C6—C2—C3117.66 (16)O1—C7—C8107.95 (14)
C6—C2—C1123.43 (17)O1—C7—H7A110.1
C3—C2—C1118.91 (17)C8—C7—H7A110.1
O2—C1—O1123.51 (18)O1—C7—H7B110.1
O2—C1—C2123.57 (18)C8—C7—H7B110.1
O1—C1—C2112.93 (16)H7A—C7—H7B108.4
C4—C3—C2119.25 (17)C7—C8—C8i111.34 (19)
C4—C3—H3120.4C7—C8—H8A109.4
C2—C3—H3120.4C8i—C8—H8A109.4
C2—C6—C5118.30 (18)C7—C8—H8B109.4
C2—C6—H6120.9C8i—C8—H8B109.4
C5—C6—H6120.9H8A—C8—H8B108.0
C4—N1—C5115.97 (17)N1—C5—C6124.61 (18)
N1—C4—C3124.21 (18)N1—C5—H5117.7
N1—C4—H4117.9C6—C5—H5117.7
C7—O1—C1—O20.3 (3)C3—C2—C6—C50.6 (3)
C7—O1—C1—C2179.81 (14)C1—C2—C6—C5179.81 (17)
C6—C2—C1—O2176.70 (18)C5—N1—C4—C30.3 (3)
C3—C2—C1—O23.7 (3)C2—C3—C4—N10.2 (3)
C6—C2—C1—O13.2 (2)C1—O1—C7—C8175.01 (15)
C3—C2—C1—O1176.39 (15)O1—C7—C8—C8i174.67 (17)
C6—C2—C3—C40.3 (3)C4—N1—C5—C60.6 (3)
C1—C2—C3—C4179.94 (16)C2—C6—C5—N10.7 (3)
Symmetry code: (i) x+1, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC16H16N2O4
Mr300.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.8519 (5), 10.5284 (6), 8.9121 (4)
β (°) 91.770 (5)
V3)736.39 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.35 × 0.13 × 0.04
Data collection
DiffractometerOxford Diffraction Xcalibur Eos
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2009)
Tmin, Tmax0.840, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
2431, 1303, 754
Rint0.018
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.039, 0.102, 0.87
No. of reflections1303
No. of parameters100
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.18, 0.13

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), PLATON (Spek, 2009).

 

Footnotes

Additional correspondence author, e-mail: manimaran.che@pondiuni.edu.in.

Acknowledgements

RK thanks the Centre for Bioinformatics [Funded by the Department of Biotechnology (DBT) and the Department of Information Technology (DIT)], Pondicherry University, for providing computational facilities to carry out this research work. BM thanks the Department of Science and Technology (DST), Government of India, New Delhi, for financial support. JM thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF).

References

First citationBrito, I., Vallejos, J., Bolte, M., López-Rodríguez, M. & Cárdenas, A. (2010). Acta Cryst. E66, o1015.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationOxford Diffraction (2009). CrysAlis CCD, CrysAlis RED and CrysAlis PRO. 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 citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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