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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2652.
Published online 2009 October 7. doi:  10.1107/S160053680903997X
PMCID: PMC2971078

2,2′-[Pyridine-2,6-diylbis(carbonyl­hydrazono)]dipropanoic acid N,N-dimethyl­formamide disolvate

Abstract

The complete molecule of the title compound, C13H13N5O6·2C3H7NO, is generated by crystallographic twofold rotation with an N and a C atom lying on the axis. The structure is stabilized by inter­molecular O—H(...)O hydrogen bonds.

Related literature

For the synthesis and structures of some organotin(IV) complexes of related tridentate hydrazone ligands see: Yin et al. (2008 [triangle]).

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Object name is e-65-o2652-scheme1.jpg

Experimental

Crystal data

  • C13H13N5O6·2C3H7NO
  • M r = 481.48
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2652-efi1.jpg
  • a = 19.5743 (17) Å
  • b = 10.4041 (11) Å
  • c = 11.7924 (12) Å
  • β = 107.684 (1)°
  • V = 2288.1 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 298 K
  • 0.40 × 0.39 × 0.17 mm

Data collection

  • Siemens CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.957, T max = 0.981
  • 5528 measured reflections
  • 2017 independent reflections
  • 1102 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.137
  • S = 1.00
  • 2017 reflections
  • 158 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680903997X/sj2660sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903997X/sj2660Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge the National Natural Foundation of China (20771053), the Scientific Research Fund of Liaocheng University (X081006) and the Students Science and Technology Innovation Fund of Liaocheng University (SRT08031HX2).

supplementary crystallographic information

Comment

Recently, we have reported some organotin(IV) complexes with hydrazone ligands (Yin et al., 2008). As an extension of our work on the structural characterization of hydrazone compounds, the title compound, (I), is reported here.

The two halves of the main molecule are symmetrically related, Fig. 1, with the N1, C4 and H4 atoms of the pyridine ring lying on the two-fold axis to form a helical species. The N3═C6 bond length of 1.283 (3) Å (Table 1) conforms to the value for a double bond, while the N2—C1 [1.361 (3) Å] and N2—N3 [1.369 (3) Å] bonds are intermediate between a double bond and a single bond because of conjugation effects in the molecule.

Experimental

Compound (I) was synthesized by the reaction of pyridine-2,6-dihydrazide (5 mmol) with pyruvic acid (10 mmol). Single crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an N,N-dimethylformamide solution.

Refinement

The H atoms were positioned geometrically, with methyl C—H distances of 0.96 Å, aromatic and aldehydic C—H distances of 0.93 Å, N—H distances of 0.86 Å and O—H distances of 0.82 Å, and refined as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C, N) or 1.5 Ueq(C, O) for the methyl groups.

Figures

Fig. 1.
The structure of the title compound, with 50% probability displacement ellipsoids and hydrogen bonds drawn as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.

Crystal data

C13H13N5O6·2C3H7NOF(000) = 1016
Mr = 481.48Dx = 1.398 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1027 reflections
a = 19.5743 (17) Åθ = 2.2–21.9°
b = 10.4041 (11) ŵ = 0.11 mm1
c = 11.7924 (12) ÅT = 298 K
β = 107.684 (1)°Block, colorless
V = 2288.1 (4) Å30.40 × 0.39 × 0.17 mm
Z = 4

Data collection

Siemens CCD area-detector diffractometer2017 independent reflections
Radiation source: fine-focus sealed tube1102 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −23→23
Tmin = 0.957, Tmax = 0.981k = −6→12
5528 measured reflectionsl = −12→14

Refinement

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) = 0.137H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0581P)2 + 0.8585P] where P = (Fo2 + 2Fc2)/3
2017 reflections(Δ/σ)max = 0.004
158 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.14 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
N10.50000.2225 (3)0.75000.0370 (8)
N20.56173 (12)0.3597 (2)0.6173 (2)0.0440 (6)
H20.54540.38940.67210.053*
N30.58981 (11)0.4428 (2)0.55325 (18)0.0414 (6)
N40.71491 (12)1.0005 (2)0.3217 (2)0.0492 (7)
O10.58033 (11)0.18075 (19)0.52026 (18)0.0608 (6)
O20.62171 (12)0.76940 (19)0.54017 (18)0.0615 (6)
O30.64206 (11)0.60873 (17)0.43031 (16)0.0539 (6)
H30.65700.66690.39720.081*
O40.69084 (11)0.78824 (19)0.32604 (17)0.0546 (6)
C10.55919 (15)0.2310 (3)0.5960 (2)0.0414 (7)
C20.52726 (14)0.1563 (2)0.6765 (2)0.0365 (7)
C30.52768 (15)0.0235 (3)0.6730 (2)0.0472 (7)
H3A0.5462−0.01990.61990.057*
C40.5000−0.0427 (4)0.75000.0550 (12)
H40.5000−0.13200.75000.066*
C50.62039 (14)0.6566 (3)0.5162 (2)0.0417 (7)
C60.59176 (14)0.5610 (3)0.5853 (2)0.0394 (7)
C70.56634 (16)0.6134 (3)0.6825 (3)0.0569 (9)
H7A0.51510.60580.66100.085*
H7B0.57970.70230.69500.085*
H7C0.58780.56600.75440.085*
C80.69523 (15)0.8983 (3)0.3682 (3)0.0502 (8)
H80.68360.90880.43850.060*
C90.73224 (17)0.9912 (3)0.2111 (3)0.0645 (10)
H9A0.72450.90460.18180.097*
H9B0.78161.01410.22460.097*
H9C0.70211.04860.15360.097*
C100.7204 (2)1.1255 (3)0.3783 (3)0.0787 (11)
H10A0.69871.12200.44120.118*
H10B0.69611.18840.32060.118*
H10C0.77001.14880.41060.118*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0357 (18)0.0301 (17)0.0426 (18)0.0000.0078 (15)0.000
N20.0566 (16)0.0331 (13)0.0493 (14)−0.0003 (12)0.0264 (12)0.0034 (11)
N30.0420 (14)0.0390 (14)0.0456 (14)0.0005 (12)0.0170 (11)0.0080 (12)
N40.0583 (16)0.0443 (14)0.0490 (15)−0.0039 (13)0.0222 (13)0.0069 (13)
O10.0845 (16)0.0466 (13)0.0638 (14)−0.0028 (12)0.0410 (12)−0.0082 (11)
O20.0899 (17)0.0351 (12)0.0710 (15)−0.0122 (12)0.0419 (13)−0.0040 (11)
O30.0756 (14)0.0412 (12)0.0559 (13)−0.0021 (11)0.0360 (11)0.0046 (10)
O40.0693 (14)0.0457 (13)0.0542 (13)−0.0067 (11)0.0268 (11)0.0046 (11)
C10.0444 (17)0.0342 (16)0.0452 (17)0.0023 (14)0.0129 (14)−0.0011 (14)
C20.0395 (16)0.0276 (15)0.0402 (16)0.0001 (13)0.0089 (13)−0.0028 (13)
C30.0542 (19)0.0338 (16)0.0558 (19)0.0004 (15)0.0202 (15)−0.0081 (15)
C40.075 (3)0.025 (2)0.073 (3)0.0000.034 (3)0.000
C50.0407 (17)0.0444 (19)0.0420 (17)−0.0004 (15)0.0154 (14)0.0015 (14)
C60.0404 (17)0.0343 (16)0.0459 (16)0.0010 (14)0.0169 (13)0.0038 (14)
C70.075 (2)0.0429 (18)0.065 (2)−0.0003 (17)0.0401 (18)−0.0006 (16)
C80.055 (2)0.054 (2)0.0442 (17)−0.0059 (17)0.0193 (15)0.0034 (16)
C90.081 (2)0.062 (2)0.057 (2)−0.0082 (19)0.0322 (18)0.0150 (17)
C100.108 (3)0.048 (2)0.093 (3)−0.009 (2)0.049 (2)−0.008 (2)

Geometric parameters (Å, °)

N1—C2i1.339 (3)C3—C41.375 (3)
N1—C21.339 (3)C3—H3A0.9300
N2—C11.361 (3)C4—C3i1.375 (3)
N2—N31.369 (3)C4—H40.9300
N2—H20.8600C5—C61.499 (4)
N3—C61.283 (3)C6—C71.485 (4)
N4—C81.308 (3)C7—H7A0.9600
N4—C91.447 (3)C7—H7B0.9600
N4—C101.451 (4)C7—H7C0.9600
O1—C11.211 (3)C8—H80.9300
O2—C51.205 (3)C9—H9A0.9600
O3—C51.310 (3)C9—H9B0.9600
O3—H30.8200C9—H9C0.9600
O4—C81.241 (3)C10—H10A0.9600
C1—C21.503 (4)C10—H10B0.9600
C2—C31.382 (4)C10—H10C0.9600
C2i—N1—C2118.0 (3)N3—C6—C7126.3 (2)
C1—N2—N3121.2 (2)N3—C6—C5117.3 (2)
C1—N2—H2119.4C7—C6—C5116.4 (2)
N3—N2—H2119.4C6—C7—H7A109.5
C6—N3—N2115.1 (2)C6—C7—H7B109.5
C8—N4—C9120.2 (3)H7A—C7—H7B109.5
C8—N4—C10121.7 (3)C6—C7—H7C109.5
C9—N4—C10118.0 (3)H7A—C7—H7C109.5
C5—O3—H3109.5H7B—C7—H7C109.5
O1—C1—N2124.0 (3)O4—C8—N4125.1 (3)
O1—C1—C2123.0 (2)O4—C8—H8117.4
N2—C1—C2113.0 (2)N4—C8—H8117.4
N1—C2—C3122.8 (3)N4—C9—H9A109.5
N1—C2—C1117.8 (2)N4—C9—H9B109.5
C3—C2—C1119.4 (2)H9A—C9—H9B109.5
C4—C3—C2118.3 (3)N4—C9—H9C109.5
C4—C3—H3A120.9H9A—C9—H9C109.5
C2—C3—H3A120.9H9B—C9—H9C109.5
C3—C4—C3i119.9 (4)N4—C10—H10A109.5
C3—C4—H4120.1N4—C10—H10B109.5
C3i—C4—H4120.1H10A—C10—H10B109.5
O2—C5—O3124.2 (3)N4—C10—H10C109.5
O2—C5—C6120.3 (3)H10A—C10—H10C109.5
O3—C5—C6115.5 (2)H10B—C10—H10C109.5

Symmetry codes: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O40.821.752.574 (3)178

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2660).

References

  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yin, H., Cui, J. & Qiao, Y. (2008). Polyhedron, 27, 2157–2166.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography