organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

4,4′-Bi­pyridine–di­methyl­glyoxime (1/1)

aCollege of Chemical Engineering,Qinghai University, Xining 810016, People's Republic of China
*Correspondence e-mail: yyan217@163.com

(Received 14 November 2011; accepted 17 December 2011; online 23 December 2011)

In the title compound, C10H8N2·C4H8N2O2, both the dimethyl­glyoxime and the 4,4′-bipyridine mol­ecules have crystallographic Ci symmetry. The mol­ecules stack along the a-axis direction with a dihedral angle of 20.4 (8)° between their planes. In the crystal, the components are linked by O—H⋯N hydrogen bonds into alternating chains along [120] and [1[\overline2]0].

Related literature

For the coordination modes of dimethyl­glyoxime, see: Malin­ovskii et al. (2004[Malinovskii, S. T., Bologa, O. A., Coropceanu, E. B., Luboradzki, R. & Gerbeleu, N. V. (2004). Russ. J. Coord. Chem. 30, 339-345.]); Coropceanu et al. (2009[Coropceanu, E., Croitor, L., Gdaniec, M., Wicher, B. & Fonari, M. (2009). Inorg. Chim. Acta, 362, 2151-2158.]). For its use in mediate magnetic inter­actions, see: Cervera et al. (1997[Cervera, B., Ruiz, R., Lloret, F., Julve, M., Cano, J., Faus, J., Bois, C. & Mrozinski, J. (1997). J. Chem. Soc. Dalton Trans. pp. 395-401.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N2·C4H8N2O2

  • Mr = 272.31

  • Monoclinic, P 21 /c

  • a = 8.7247 (17) Å

  • b = 7.1486 (14) Å

  • c = 11.502 (2) Å

  • β = 99.44 (3)°

  • V = 707.6 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 298 K

  • 0.20 × 0.18 × 0.15 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.982, Tmax = 0.987

  • 9684 measured reflections

  • 1636 independent reflections

  • 1265 reflections with I > 2σ(I)

  • Rint = 0.040

Refinement
  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.133

  • S = 1.05

  • 1636 reflections

  • 93 parameters

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.13 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1i 0.82 1.94 2.7459 (17) 169
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Dimethylglyoxime (H2dmg) with its two oximate group (N–O–) is a suitable scaffold to construct metal-containing building blocks for extended supramolecular architectures. Several complexes of transition metals with this ligand and its derivatives have been reported (Malinovskii et al., 2004; Coropceanu et al., 2009). Moreover, the NO oxime group has a remarkable efficiency to mediate magnetic interactions when it acts as a bridging ligand (Cervera et al., 1997).

Starting from Mn(CH3COO)2 and H2dmg, and using 4,4'-dpy as a bridging ligand, we have aimed to prepare a complex with superior magnetic properties. However, the reaction resulted in a stoichiometric (1:1) molecular complex of dimethylglyoxime-4,4'-bipyridine.

In this structure, the molecules of H2dmg and 4,4'-dpy are linked through O—H···N hydrogen bonds into alternating chains (Fig. 2).

Related literature top

For the coordination modes of dimethylglyoxime, see: Malinovskii et al. (2004); Coropceanu et al. (2009). For its use in mediate magnetic interactions, see: Cervera et al. (1997).

Experimental top

Mn(CH3COO)2.4H2O (0.025 g, 0.1 mmol) in 5 ml of water and CH3COONa(0.016 g, 0.2 mmol) were added to a mixture of H2dmg (0.024 g, 0.2 mmol) and 4,4'-dpy in 10 ml of methanol. The reaction mixture was boiled in a crucible for ~10 min. The solvent was then evaporated and colorless crystals of the title compound were obtained.

Refinement top

Methyl H atoms were placed in calculated position with C—H=0.96 Å, and torsion angles were refined, Uiso(H)=1.5Ueq(C). The position of the O-bound H-atom was determined from a difference Fourier map and then geometrically restrained with O—H=0.82 Å, and Uiso(H)=1.5Ueq(O). Aromatic H atoms were placed in calculated positions with C—H=0.93Å and refined in riding mode with Uiso(H)=1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Heterosoric stacks of the molecules.
4,4'-Bipyridine–dimethylglyoxime (1/1) top
Crystal data top
C10H8N2·C4H8N2O2F(000) = 288
Mr = 272.31707.6(2)
Monoclinic, P21/cDx = 1.278 Mg m3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 8.7247 (17) ÅCell parameters from 1636 reflections
b = 7.1486 (14) Åθ = 2.4–27.5°
c = 11.502 (2) ŵ = 0.09 mm1
β = 99.44 (3)°T = 298 K
V = 707.6 (2) Å3Block, colourless
Z = 20.20 × 0.18 × 0.15 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
1636 independent reflections
Radiation source: fine-focus sealed tube1265 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
ϕ and ω scansθmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1111
Tmin = 0.982, Tmax = 0.987k = 99
9684 measured reflectionsl = 1414
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.062P)2 + 0.1229P]
where P = (Fo2 + 2Fc2)/3
1636 reflections(Δ/σ)max = 0.021
93 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = 0.13 e Å3
Crystal data top
C10H8N2·C4H8N2O2V = 707.6 (2) Å3
Mr = 272.31Z = 2
Monoclinic, P21/cMo Kα radiation
a = 8.7247 (17) ŵ = 0.09 mm1
b = 7.1486 (14) ÅT = 298 K
c = 11.502 (2) Å0.20 × 0.18 × 0.15 mm
β = 99.44 (3)°
Data collection top
Bruker SMART APEX CCD
diffractometer
1636 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
1265 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.987Rint = 0.040
9684 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.05Δρmax = 0.19 e Å3
1636 reflectionsΔρmin = 0.13 e Å3
93 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
C10.02851 (14)0.09220 (19)0.48302 (12)0.0464 (3)
O10.72158 (14)0.26180 (17)0.14282 (10)0.0699 (4)
H10.77400.17140.12960.105*
N10.14118 (15)0.43625 (18)0.41432 (12)0.0600 (4)
N20.62500 (14)0.31488 (17)0.03926 (12)0.0556 (4)
C50.04603 (17)0.1905 (2)0.38632 (14)0.0557 (4)
H50.13640.14290.34210.067*
C60.55111 (16)0.4662 (2)0.05327 (13)0.0518 (4)
C30.21126 (19)0.3451 (2)0.50901 (16)0.0652 (5)
H30.29970.39820.55270.078*
C20.16017 (18)0.1766 (2)0.54594 (15)0.0591 (4)
H20.21370.11900.61300.071*
C40.01328 (18)0.3583 (2)0.35553 (15)0.0605 (4)
H40.03910.42080.28990.073*
C70.5661 (2)0.5712 (3)0.16681 (15)0.0701 (5)
H7A0.54140.48970.22750.105*
H7B0.49580.67540.15780.105*
H7C0.67070.61580.18810.105*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0428 (7)0.0475 (7)0.0486 (7)0.0018 (5)0.0062 (5)0.0049 (6)
O10.0727 (8)0.0700 (8)0.0608 (7)0.0253 (6)0.0076 (6)0.0006 (5)
N10.0600 (8)0.0521 (7)0.0671 (8)0.0065 (6)0.0081 (6)0.0017 (6)
N20.0527 (7)0.0553 (7)0.0560 (7)0.0087 (5)0.0001 (5)0.0000 (5)
C50.0513 (8)0.0572 (8)0.0550 (8)0.0064 (6)0.0020 (6)0.0017 (7)
C60.0473 (7)0.0539 (8)0.0529 (8)0.0050 (6)0.0042 (6)0.0030 (6)
C30.0583 (9)0.0607 (9)0.0723 (11)0.0125 (7)0.0024 (8)0.0045 (8)
C20.0548 (8)0.0562 (9)0.0614 (9)0.0035 (7)0.0049 (7)0.0018 (7)
C40.0621 (9)0.0570 (9)0.0596 (9)0.0021 (7)0.0020 (7)0.0063 (7)
C70.0760 (11)0.0732 (11)0.0567 (9)0.0180 (9)0.0026 (8)0.0097 (8)
Geometric parameters (Å, º) top
C1—C51.384 (2)C6—C6ii1.474 (3)
C1—C21.391 (2)C6—C71.493 (2)
C1—C1i1.484 (3)C3—C21.376 (2)
O1—N21.3941 (17)C3—H30.9300
O1—H10.8200C2—H20.9300
N1—C41.329 (2)C4—H40.9300
N1—C31.329 (2)C7—H7A0.9600
N2—C61.2831 (18)C7—H7B0.9600
C5—C41.376 (2)C7—H7C0.9600
C5—H50.9300
C5—C1—C2115.92 (14)C2—C3—H3118.2
C5—C1—C1i121.91 (15)C3—C2—C1120.06 (15)
C2—C1—C1i122.16 (16)C3—C2—H2120.0
N2—O1—H1109.5C1—C2—H2120.0
C4—N1—C3116.54 (14)N1—C4—C5123.68 (15)
C6—N2—O1111.59 (12)N1—C4—H4118.2
C4—C5—C1120.16 (14)C5—C4—H4118.2
C4—C5—H5119.9C6—C7—H7A109.5
C1—C5—H5119.9C6—C7—H7B109.5
N2—C6—C6ii114.82 (16)H7A—C7—H7B109.5
N2—C6—C7124.04 (14)C6—C7—H7C109.5
C6ii—C6—C7121.13 (16)H7A—C7—H7C109.5
N1—C3—C2123.61 (14)H7B—C7—H7C109.5
N1—C3—H3118.2
C2—C1—C5—C41.8 (2)N1—C3—C2—C10.1 (3)
C1i—C1—C5—C4177.95 (15)C5—C1—C2—C31.7 (2)
O1—N2—C6—C6ii178.74 (15)C1i—C1—C2—C3178.06 (16)
O1—N2—C6—C70.5 (2)C3—N1—C4—C51.3 (2)
C4—N1—C3—C21.4 (3)C1—C5—C4—N10.3 (3)
Symmetry codes: (i) x, y, z+1; (ii) x+1, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1iii0.821.942.7459 (17)169
Symmetry code: (iii) x+1, y1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H8N2·C4H8N2O2
Mr272.31
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)8.7247 (17), 7.1486 (14), 11.502 (2)
β (°) 99.44 (3)
V3)707.6 (2)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.18 × 0.15
Data collection
DiffractometerBruker SMART APEX CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.982, 0.987
No. of measured, independent and
observed [I > 2σ(I)] reflections
9684, 1636, 1265
Rint0.040
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.133, 1.05
No. of reflections1636
No. of parameters93
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.13

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.821.942.7459 (17)168.7
Symmetry code: (i) x+1, y1/2, z+1/2.
 

Acknowledgements

This work was supported by the Qinghai Province International Science and Technology Cooperation Plan Projects (2011-H-808).

References

First citationBruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.
First citationCervera, B., Ruiz, R., Lloret, F., Julve, M., Cano, J., Faus, J., Bois, C. & Mrozinski, J. (1997). J. Chem. Soc. Dalton Trans. pp. 395–401.  CSD CrossRef Web of Science
First citationCoropceanu, E., Croitor, L., Gdaniec, M., Wicher, B. & Fonari, M. (2009). Inorg. Chim. Acta, 362, 2151–2158.  CrossRef CAS
First citationMalinovskii, S. T., Bologa, O. A., Coropceanu, E. B., Luboradzki, R. & Gerbeleu, N. V. (2004). Russ. J. Coord. Chem. 30, 339–345.  CrossRef CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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