4,4′-Bipyridine acetic acid disolvate

Ye, L.

doi:10.1107/S1600536807062319

organic compounds

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Volume 64| Part 1| January 2008| Page o46

https://doi.org/10.1107/S1600536807062319

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4,4′-Bipyridine acetic acid disolvate

Ling Ye ^a ^*

^aState Key Laboratory of Supramolecular Structure and Materials, Jilin University, Changchun 130012, People's Republic of China
^*Correspondence e-mail: xray@jlu.edu.cn

(Received 12 November 2007; accepted 22 November 2007; online 6 December 2007)

The crystal structure of the title compound, C₁₀H₈N₂·2C₂H₄O₂, is built up from 4,4′-bipyridine and acetic acid molecules linked by strong O—H⋯N hydrogen bonds. The 4,4′-bipyridine and the two acetic acid molecules are further connected through weak C—H⋯O hydrogen bonds to form a supramolecular two-dimensional network parallel to the (001) plane. The two pyridine rings make a dihedral angle of 31.8 (1)°.

Related literature

For related literature, see: Dai et al. (2005 ); Li et al. (2005 ); Pedireddi et al. (1998 ); Wang et al. (2006 ). For structural analysis, see: Spek (2003 ).

Experimental

Crystal data

C₁₀H₈N₂·2C₂H₄O₂
M_r = 276.29
Monoclinic, P c
a = 3.893 (2) Å
b = 8.181 (5) Å
c = 22.563 (15) Å
β = 98.46 (3)°
V = 710.7 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 291 (2) K
0.15 × 0.13 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.986, T_max = 0.988
6467 measured reflections
1595 independent reflections
995 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.119
S = 1.04
1595 reflections
185 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.86	2.675 (5)	175
O4—H4A⋯N1	0.82	1.84	2.659 (5)	173
C7—H7⋯O1ⁱ	0.93	2.62	3.526 (5)	165
C10—H10⋯O3ⁱⁱ	0.93	2.37	3.273 (5)	164
C4—H4⋯O3ⁱⁱⁱ	0.93	2.56	3.397 (6)	150
Symmetry codes: (i) x-1, y-1, z; (ii) x+1, y+1, z; (iii) x, y+1, z.

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ); ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807062319/dn2279sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807062319/dn2279Isup2.hkl

checkCIF report

Comment top

2,2-bipyridine is widely used to build up supramolecular network with carboxylic acid (Dai et al., 2005; Li et al., 2005; Pedireddi et al., 1998; Wang et al., 2006). Herein, we report the co-crystal structure of 2,2-bipyridine and acetic acid.

The asymmetric unit of (I) contains one 4,4-bipyridine molecule and two acetic acid molecules linked trough strong O—H···O hydogen bonds (Fig. 1). The two pyridine rings are both planar, with a RMS deviation of fitted atoms being 0.0033 Å and 0.0074 Å, respectively. The dihedral angle between them is 31.8 (1) °.

The 4,4-bipyridine and the two acetic acid molecules are further connected through C—H···O weak hydrogen bonds (PLATON, Spek, 2003) involving the carboxyl oxygen atoms (Table 1) to build up a supramolecular two dimensionnal network.parallel to the (0 0 1) plane (Fig. 2).

Related literature top

For related literature, see: Dai et al. (2005); Li et al. (2005); Pedireddi et al. (1998); Wang et al. (2006). For strutural analysis, se: Spek (2003).

Experimental top

A mixture of 2,2-bipyridine (5 mmol, 0.78 g) and acetic acid (10 mmol, 0.60 g) in water (10 ml) was stirred for 2 h, and filtrate was allowed to evaporate at room temperature. Colorless single crystals of the title compound were formed after two weeks.

Structure description top

For related literature, see: Dai et al. (2005); Li et al. (2005); Pedireddi et al. (1998); Wang et al. (2006). For strutural analysis, se: Spek (2003).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The asymmetric unit, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Packing view showing the Hydrogen bonding network. H atoms not involved in hydrogen bonds have been omitted for clarity.

4,4-Bipyridine acetic acid disolvate top

Crystal data top

C₁₀H₈N₂·2C₂H₄O₂	F(000) = 292
M_r = 276.29	D_x = 1.291 Mg m⁻³
Monoclinic, Pc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2yc	Cell parameters from 4188 reflections
a = 3.893 (2) Å	θ = 3.1–27.5°
b = 8.181 (5) Å	µ = 0.10 mm⁻¹
c = 22.563 (15) Å	T = 291 K
β = 98.46 (3)°	Block, colorless
V = 710.7 (7) Å³	0.15 × 0.13 × 0.12 mm
Z = 2

Data collection top

Rigaku RAXIS-RAPID diffractometer	1595 independent reflections
Radiation source: fine-focus sealed tube	995 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −5→5
T_min = 0.986, T_max = 0.988	k = −10→10
6467 measured reflections	l = −29→24

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0545P)² + 0.0575P] where P = (F_o² + 2F_c²)/3
1595 reflections	(Δ/σ)_max = 0.003
185 parameters	Δρ_max = 0.15 e Å⁻³
2 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₁₀H₈N₂·2C₂H₄O₂	V = 710.7 (7) Å³
M_r = 276.29	Z = 2
Monoclinic, Pc	Mo Kα radiation
a = 3.893 (2) Å	µ = 0.10 mm⁻¹
b = 8.181 (5) Å	T = 291 K
c = 22.563 (15) Å	0.15 × 0.13 × 0.12 mm
β = 98.46 (3)°

Data collection top

Rigaku RAXIS-RAPID diffractometer	1595 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	995 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.988	R_int = 0.042
6467 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	2 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.04	Δρ_max = 0.15 e Å⁻³
1595 reflections	Δρ_min = −0.13 e Å⁻³
185 parameters

Special details top

Experimental. (See detailed section in the paper)

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

	x	y	z	U_iso*/U_eq
C13	−0.0181 (13)	−0.0149 (6)	0.6249 (2)	0.0728 (12)
H13A	0.1830	−0.0660	0.6470	0.109*
H13B	−0.1649	−0.0968	0.6039	0.109*
H13C	−0.1437	0.0423	0.6521	0.109*
C14	0.0919 (10)	0.1019 (5)	0.5814 (2)	0.0568 (10)
C1	0.4437 (12)	0.3978 (5)	0.47047 (19)	0.0697 (11)
H1	0.4572	0.2861	0.4636	0.084*
C2	0.4896 (13)	0.5031 (5)	0.4247 (2)	0.0640 (10)
H2	0.5306	0.4622	0.3879	0.077*
C3	0.4742 (9)	0.6695 (4)	0.43371 (16)	0.0488 (9)
C4	0.4131 (11)	0.7207 (5)	0.48979 (19)	0.0613 (11)
H4	0.4020	0.8316	0.4984	0.074*
C5	0.3695 (12)	0.6071 (5)	0.5321 (2)	0.0690 (12)
H5	0.3285	0.6441	0.5694	0.083*
C6	0.5176 (9)	0.7891 (4)	0.38616 (17)	0.0483 (9)
C7	0.4150 (11)	0.7538 (5)	0.32659 (19)	0.0599 (11)
H7	0.3218	0.6520	0.3152	0.072*
C8	0.4513 (11)	0.8706 (5)	0.2839 (2)	0.0654 (11)
H8	0.3770	0.8449	0.2440	0.078*
C9	0.6937 (12)	1.0494 (5)	0.35465 (19)	0.0649 (11)
H9	0.7942	1.1507	0.3646	0.078*
C10	0.6649 (11)	0.9422 (5)	0.39995 (18)	0.0599 (10)
H10	0.7426	0.9709	0.4395	0.072*
N1	0.3818 (10)	0.4468 (4)	0.52352 (16)	0.0655 (9)
O1	0.9176 (9)	1.3967 (4)	0.29266 (15)	0.0859 (11)
O3	0.0627 (10)	0.0786 (4)	0.52832 (15)	0.0938 (11)
C11	0.8647 (13)	1.5081 (6)	0.1948 (2)	0.0764 (14)
H11A	1.0155	1.5926	0.2131	0.115*
H11B	0.6438	1.5545	0.1789	0.115*
H11C	0.9664	1.4585	0.1630	0.115*
C12	0.8156 (11)	1.3817 (4)	0.2405 (2)	0.0565 (10)
N2	0.5861 (9)	1.0176 (4)	0.29663 (16)	0.0631 (9)
O2	0.6441 (8)	1.2545 (3)	0.21698 (13)	0.0698 (8)
H2A	0.6294	1.1864	0.2432	0.105*
O4	0.2338 (8)	0.2354 (3)	0.60567 (13)	0.0711 (9)
H4A	0.2902	0.2947	0.5794	0.107*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C13	0.074 (3)	0.066 (3)	0.075 (3)	−0.009 (2)	0.001 (2)	0.010 (2)
C14	0.056 (2)	0.051 (2)	0.061 (3)	0.0012 (18)	0.0008 (19)	−0.005 (2)
C1	0.097 (3)	0.050 (2)	0.063 (3)	0.005 (2)	0.013 (2)	0.004 (2)
C2	0.082 (3)	0.053 (2)	0.057 (2)	0.002 (2)	0.0112 (19)	0.000 (2)
C3	0.049 (2)	0.0470 (19)	0.049 (2)	0.0035 (17)	0.0013 (16)	0.0002 (17)
C4	0.078 (3)	0.048 (2)	0.058 (3)	0.0023 (19)	0.012 (2)	0.0001 (19)
C5	0.083 (3)	0.070 (3)	0.054 (2)	0.003 (2)	0.013 (2)	−0.001 (2)
C6	0.0467 (19)	0.0427 (18)	0.055 (2)	−0.0021 (16)	0.0050 (16)	0.0016 (17)
C7	0.075 (3)	0.048 (2)	0.054 (2)	−0.0082 (19)	0.003 (2)	0.002 (2)
C8	0.080 (3)	0.056 (2)	0.058 (2)	−0.009 (2)	0.004 (2)	0.000 (2)
C9	0.075 (3)	0.048 (2)	0.070 (3)	−0.0104 (19)	0.003 (2)	−0.002 (2)
C10	0.069 (3)	0.051 (2)	0.056 (2)	−0.0030 (19)	−0.001 (2)	−0.0051 (19)
N1	0.077 (2)	0.058 (2)	0.062 (2)	−0.0027 (17)	0.0123 (17)	0.0040 (18)
O1	0.119 (3)	0.072 (2)	0.062 (2)	−0.0298 (19)	−0.0012 (19)	−0.0039 (17)
O3	0.143 (3)	0.076 (2)	0.059 (2)	−0.021 (2)	0.002 (2)	−0.0126 (18)
C11	0.079 (3)	0.067 (3)	0.083 (4)	−0.012 (2)	0.008 (2)	0.015 (2)
C12	0.067 (3)	0.044 (2)	0.059 (3)	−0.0042 (19)	0.010 (2)	0.000 (2)
N2	0.076 (2)	0.0469 (19)	0.065 (2)	−0.0092 (16)	0.0076 (17)	0.0014 (17)
O2	0.096 (2)	0.0558 (17)	0.0559 (18)	−0.0206 (16)	0.0061 (16)	−0.0045 (13)
O4	0.098 (2)	0.0591 (18)	0.0567 (19)	−0.0146 (16)	0.0117 (16)	−0.0058 (14)

Geometric parameters (Å, º) top

C13—C14	1.478 (6)	C6—C10	1.393 (5)
C13—H13A	0.9600	C7—C8	1.378 (6)
C13—H13B	0.9600	C7—H7	0.9300
C13—H13C	0.9600	C8—N2	1.326 (5)
C14—O3	1.201 (5)	C8—H8	0.9300
C14—O4	1.307 (5)	C9—N2	1.340 (5)
C1—N1	1.317 (6)	C9—C10	1.364 (6)
C1—C2	1.377 (6)	C9—H9	0.9300
C1—H1	0.9300	C10—H10	0.9300
C2—C3	1.380 (5)	O1—C12	1.191 (5)
C2—H2	0.9300	C11—C12	1.493 (6)
C3—C4	1.386 (6)	C11—H11A	0.9600
C3—C6	1.480 (5)	C11—H11B	0.9600
C4—C5	1.361 (6)	C11—H11C	0.9600
C4—H4	0.9300	C12—O2	1.306 (4)
C5—N1	1.328 (5)	O2—H2A	0.8200
C5—H5	0.9300	O4—H4A	0.8200
C6—C7	1.375 (5)

C14—C13—H13A	109.5	C10—C6—C3	121.3 (3)
C14—C13—H13B	109.5	C6—C7—C8	119.5 (4)
H13A—C13—H13B	109.5	C6—C7—H7	120.3
C14—C13—H13C	109.5	C8—C7—H7	120.3
H13A—C13—H13C	109.5	N2—C8—C7	123.8 (4)
H13B—C13—H13C	109.5	N2—C8—H8	118.1
O3—C14—O4	121.5 (4)	C7—C8—H8	118.1
O3—C14—C13	124.4 (4)	N2—C9—C10	124.0 (4)
O4—C14—C13	114.0 (4)	N2—C9—H9	118.0
N1—C1—C2	123.6 (4)	C10—C9—H9	118.0
N1—C1—H1	118.2	C9—C10—C6	119.2 (4)
C2—C1—H1	118.2	C9—C10—H10	120.4
C1—C2—C3	119.5 (4)	C6—C10—H10	120.4
C1—C2—H2	120.2	C1—N1—C5	116.6 (4)
C3—C2—H2	120.2	C12—C11—H11A	109.5
C2—C3—C4	116.8 (4)	C12—C11—H11B	109.5
C2—C3—C6	122.2 (3)	H11A—C11—H11B	109.5
C4—C3—C6	121.0 (3)	C12—C11—H11C	109.5
C5—C4—C3	119.4 (4)	H11A—C11—H11C	109.5
C5—C4—H4	120.3	H11B—C11—H11C	109.5
C3—C4—H4	120.3	O1—C12—O2	124.1 (4)
N1—C5—C4	124.1 (4)	O1—C12—C11	123.6 (4)
N1—C5—H5	117.9	O2—C12—C11	112.3 (4)
C4—C5—H5	117.9	C8—N2—C9	116.3 (4)
C7—C6—C10	117.3 (3)	C12—O2—H2A	109.5
C7—C6—C3	121.4 (3)	C14—O4—H4A	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.86	2.675 (5)	175
O4—H4A···N1	0.82	1.84	2.659 (5)	173
C7—H7···O1ⁱ	0.93	2.62	3.526 (5)	165
C10—H10···O3ⁱⁱ	0.93	2.37	3.273 (5)	164
C4—H4···O3ⁱⁱⁱ	0.93	2.56	3.397 (6)	150

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·2C₂H₄O₂
M_r	276.29
Crystal system, space group	Monoclinic, Pc
Temperature (K)	291
a, b, c (Å)	3.893 (2), 8.181 (5), 22.563 (15)
β (°)	98.46 (3)
V (Å³)	710.7 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.15 × 0.13 × 0.12

Data collection
Diffractometer	Rigaku RAXIS-RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.986, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	6467, 1595, 995
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.119, 1.04
No. of reflections	1595
No. of parameters	185
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.13

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.86	2.675 (5)	174.5
O4—H4A···N1	0.82	1.84	2.659 (5)	173.1
C7—H7···O1ⁱ	0.93	2.62	3.526 (5)	165.2
C10—H10···O3ⁱⁱ	0.93	2.37	3.273 (5)	164.3
C4—H4···O3ⁱⁱⁱ	0.93	2.56	3.397 (6)	150.0

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

References

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