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Acta Crystallogr Sect E Struct Rep Online. 2009 August 1; 65(Pt 8): o1825.
Published online 2009 July 11. doi:  10.1107/S1600536809026488
PMCID: PMC2977368

2-{5-[N-(2-Pyridyl)carbamo­yl]pentan­amido}pyridinium hexa­fluoro­phosphate

Abstract

In the crystal structure of the title compound, C16H19N4O2 +·PF6 , the cations and anions are situated on centres of inversion. Thus, the N—H H atom is disordered over both N atoms due to symmetry. In the crystal, mol­ecules are connected via N—H(...)F and N—H(...)O hydrogen bonds. The cation adopts the (...)AAA(...) trans conformation in the solid state.

Related literature

For similar structures, see: Chen et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1825-scheme1.jpg

Experimental

Crystal data

  • C16H19N4O2 +·PF6
  • M r = 444.32
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1825-efi1.jpg
  • a = 6.2119 (18) Å
  • b = 12.9265 (11) Å
  • c = 11.439 (2) Å
  • β = 96.415 (10)°
  • V = 912.8 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.23 mm−1
  • T = 295 K
  • 0.5 × 0.2 × 0.2 mm

Data collection

  • Bruker P4 diffractometer
  • Absorption correction: multi-scan (XSCANS; Siemens, 1995 [triangle]) T min = 0.945, T max = 0.962
  • 2288 measured reflections
  • 1612 independent reflections
  • 1334 reflections with I > 2σ(I)
  • R int = 0.020
  • 3 standard reflections every 97 reflections intensity decay: none

Refinement

  • R[F 2 > 2σ(F 2)] = 0.036
  • wR(F 2) = 0.096
  • S = 1.07
  • 1612 reflections
  • 133 parameters
  • H-atom parameters constrained
  • Δρmax = 0.40 e Å−3
  • Δρmin = −0.30 e Å−3

Data collection: XSCANS (Siemens, 1995 [triangle]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL; 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/S1600536809026488/nc2150sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026488/nc2150Isup2.hkl

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

Acknowledgments

We are grateful to the National Science Council of the Republic of China for support. This research was also supported by the project of specific research fields in Chung-Yuan Christian University, Taiwan, under grant CYCU-97-CR-CH.

supplementary crystallographic information

Comment

The compound N1,N2-di(2-pyridyl)adipoamide has been used as bridging ligand in coordination chemistry (Chen et al., 2007). In the present work the structure of the title compound (Fig. 1) has been determined to investigate the role of the cation-anion interaction on the ligand conformation. The molecules are connected via N—H···F and N—H···O hydrogen bonds (Tab. 1). The cation adopts the AAA trans conformation in the solid state. This conformation is the same as that found for the neutral N1,N2-di(2-pyridyl)adipoamide ligand which cocrystallize with water (Chen et al., 2007).

Experimental

N1,N2-Di(2-pyridyl)adipoamide (0.30 g, 1.00 mmol) and AgPF6 (0.25 g, 1.00 mmol) were placed in a flask containing 20 ml of CH2Cl2. The mixture was refluxed for 8 h to give a white precipitate, which was then filtered and dried under vacuum. By dissolving the solid in dichloromethane, followed by allowing the solvent to evaporate slowly under air, plate colorless crystals suitable for X-ray crystallography were obtained.

Refinement

All the hydrogen atoms were situated into idealized positions and constrained by the riding atom approximation with C—H = 0.93 — 0.97 Å, N—H = 0.86 Å and Uiso(H) = 1.2Ueq(C, N). The occupancy of the H atom H1A was set to be 0.5 to balance the charge. Because of the disorder of the N-H H atom, the structure was also refined in space group Pc and P21. However, even in these cases the disorder is still present and therefore, space group P21/c was selected.

Figures

Fig. 1.
The title molecule with the labelling scheme. The bond to the disordered H atom is indicated by dashed open lines. The displacement ellipsoids are drawn at the 30% probability level.Symmetry codes: (i) -x,-y+1,-z; (ii) -x-1,-y,-z.

Crystal data

C16H19N4O2+·PF6F(000) = 456
Mr = 444.32Dx = 1.617 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 27 reflections
a = 6.2119 (18) Åθ = 5.1–12.5°
b = 12.9265 (11) ŵ = 0.23 mm1
c = 11.439 (2) ÅT = 295 K
β = 96.415 (10)°Plate, colorless
V = 912.8 (3) Å30.5 × 0.2 × 0.2 mm
Z = 2

Data collection

Bruker P4 diffractometer1334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.020
graphiteθmax = 25.0°, θmin = 2.4°
ω scansh = −1→7
Absorption correction: multi-scan (XSCANS; Siemens, 1995)k = −15→1
Tmin = 0.945, Tmax = 0.962l = −13→13
2288 measured reflections3 standard reflections every 97 reflections
1612 independent reflections intensity decay: none

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)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0403P)2 + 0.4314P] where P = (Fo2 + 2Fc2)/3
1612 reflections(Δ/σ)max < 0.001
133 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = −0.30 e Å3

Special details

Experimental. 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.
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)

xyzUiso*/UeqOcc. (<1)
P0.00000.50000.00000.0275 (2)
F10.0589 (2)0.37673 (9)−0.03443 (10)0.0367 (3)
F20.2624 (2)0.52790 (12)0.01505 (15)0.0549 (4)
F3−0.0162 (3)0.53230 (11)−0.14390 (11)0.0517 (4)
O−0.0438 (3)0.16414 (14)0.01248 (14)0.0526 (5)
N10.2814 (3)0.26186 (14)0.14024 (15)0.0331 (4)
H1A0.17770.27520.08610.040*0.50
N20.0760 (3)0.12150 (15)0.20013 (15)0.0352 (4)
H2A0.04730.08580.25990.042*
C10.4629 (4)0.32123 (18)0.1488 (2)0.0387 (5)
H1B0.47390.37490.09570.046*
C20.6283 (4)0.30293 (19)0.2341 (2)0.0410 (5)
H2B0.75330.34300.23920.049*
C30.6078 (4)0.22297 (19)0.3140 (2)0.0386 (5)
H3A0.71870.21020.37390.046*
C40.4248 (4)0.16336 (18)0.30451 (18)0.0347 (5)
H4A0.41070.11020.35790.042*
C50.2600 (3)0.18256 (16)0.21465 (17)0.0300 (5)
C6−0.0652 (4)0.11249 (17)0.09912 (19)0.0336 (5)
C7−0.2390 (4)0.03259 (18)0.10327 (19)0.0365 (5)
H7A−0.30560.04090.17550.044*
H7B−0.1743−0.03570.10410.044*
C8−0.4124 (4)0.04088 (18)−0.0011 (2)0.0375 (5)
H8A−0.47840.1089−0.00120.045*
H8B−0.34510.0339−0.07330.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P0.0269 (4)0.0280 (4)0.0265 (4)−0.0007 (3)−0.0013 (3)−0.0024 (3)
F10.0443 (7)0.0275 (6)0.0364 (6)0.0055 (6)−0.0032 (5)−0.0043 (5)
F20.0268 (7)0.0474 (8)0.0887 (12)−0.0045 (6)−0.0011 (7)−0.0043 (8)
F30.0854 (11)0.0420 (8)0.0276 (7)0.0119 (7)0.0052 (7)0.0018 (6)
O0.0577 (12)0.0553 (11)0.0398 (9)−0.0212 (9)−0.0163 (8)0.0162 (8)
N10.0326 (10)0.0340 (10)0.0319 (9)−0.0024 (8)−0.0009 (8)0.0032 (8)
N20.0315 (10)0.0448 (11)0.0282 (9)−0.0073 (9)−0.0020 (7)0.0074 (8)
C10.0428 (13)0.0332 (12)0.0395 (12)−0.0057 (10)0.0023 (10)0.0022 (10)
C20.0328 (12)0.0410 (13)0.0482 (13)−0.0077 (10)−0.0002 (10)−0.0053 (11)
C30.0307 (11)0.0445 (14)0.0381 (12)0.0037 (10)−0.0077 (9)−0.0038 (10)
C40.0333 (12)0.0385 (12)0.0305 (10)0.0014 (10)−0.0040 (9)0.0043 (9)
C50.0277 (11)0.0336 (11)0.0281 (10)0.0009 (9)0.0007 (8)0.0005 (9)
C60.0325 (11)0.0342 (11)0.0329 (11)0.0008 (9)−0.0022 (9)0.0012 (9)
C70.0367 (12)0.0382 (12)0.0330 (11)−0.0049 (10)−0.0023 (9)0.0004 (10)
C80.0353 (11)0.0362 (12)0.0394 (12)−0.0046 (10)−0.0024 (10)0.0009 (10)

Geometric parameters (Å, °)

P—F2i1.6596 (14)C1—H1B0.9300
P—F21.6596 (14)C2—C31.395 (3)
P—F31.6902 (13)C2—H2B0.9300
P—F3i1.6902 (13)C3—C41.368 (3)
P—F11.6912 (12)C3—H3A0.9300
P—F1i1.6913 (12)C4—C51.389 (3)
O—C61.214 (3)C4—H4A0.9300
N1—C51.348 (3)C6—C71.499 (3)
N1—C11.358 (3)C7—C81.520 (3)
N1—H1A0.8600C7—H7A0.9700
N2—C61.375 (3)C7—H7B0.9700
N2—C51.383 (3)C8—C8ii1.519 (4)
N2—H2A0.8600C8—H8A0.9700
C1—C21.356 (3)C8—H8B0.9700
F2i—P—F2180.0C3—C2—H2B120.5
F2i—P—F390.09 (8)C4—C3—C2120.1 (2)
F2—P—F389.91 (8)C4—C3—H3A120.0
F2i—P—F3i89.91 (8)C2—C3—H3A120.0
F2—P—F3i90.09 (8)C3—C4—C5119.7 (2)
F3—P—F3i180.00 (9)C3—C4—H4A120.2
F2i—P—F190.39 (7)C5—C4—H4A120.2
F2—P—F189.61 (7)N1—C5—N2119.76 (18)
F3—P—F189.82 (6)N1—C5—C4119.09 (19)
F3i—P—F190.18 (6)N2—C5—C4121.14 (19)
F2i—P—F1i89.61 (7)O—C6—N2121.4 (2)
F2—P—F1i90.39 (7)O—C6—C7123.3 (2)
F3—P—F1i90.18 (6)N2—C6—C7115.21 (18)
F3i—P—F1i89.82 (6)C6—C7—C8112.12 (18)
F1—P—F1i180.00 (8)C6—C7—H7A109.2
C5—N1—C1121.58 (19)C8—C7—H7A109.2
C5—N1—H1A119.2C6—C7—H7B109.2
C1—N1—H1A119.2C8—C7—H7B109.2
C6—N2—C5126.15 (18)H7A—C7—H7B107.9
C6—N2—H2A116.9C8ii—C8—C7112.6 (2)
C5—N2—H2A116.9C8ii—C8—H8A109.1
C2—C1—N1120.6 (2)C7—C8—H8A109.1
C2—C1—H1B119.7C8ii—C8—H8B109.1
N1—C1—H1B119.7C7—C8—H8B109.1
C1—C2—C3118.9 (2)H8A—C8—H8B107.8
C1—C2—H2B120.5

Symmetry codes: (i) −x, −y+1, −z; (ii) −x−1, −y, −z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···F10.861.982.737 (2)145
N1—H1A···O0.862.102.674 (2)124
N2—H2A···F3iii0.861.952.774 (2)161
N2—H2A···F1iii0.862.403.050 (2)133

Symmetry codes: (iii) x, −y+1/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NC2150).

References

  • Chen, H.-C., Hu, H.-L., Chan, Z.-K., Yeh, C.-W., Jia, H.-W., Wu, C.-P., Chen, J.-D. & Wang, J.-C. (2007). Cryst. Growth Des.7, 698–704.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1995). XSCANS Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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