2,2′-Bipyridine–cyclo­pentane-1,2,3,4-tetra­carb­oxy­lic acid (1/1)

Lin, J.-L.; Guo, X.-X.; Huang, W.-X.

doi:10.1107/S1600536811025827

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1945

doi:10.1107/S1600536811025827

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2,2′-Bipyridine–cyclopentane-1,2,3,4-tetracarboxylic acid (1/1)

Jian-Li Lin,^a ^* Xia-Xia Guo ^a and Wen-Xiang Huang ^a

^aCenter of Applied Solid State Chemistry Research, Ningbo University, Ningbo, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: linjianli@nbu.edu.cn

(Received 25 June 2011; accepted 30 June 2011; online 9 July 2011)

The asymmetric unit of the title compound, C₁₀H₈N₂·C₉H₁₀O₈, contains a half-molecule of 2,2′-bipyridine and a half-molecule of 1,2,3,4-cyclopentanetetracarboxylic acid, both components being completed by crystallographic inversion symmetry. In the crystal, the molecules are assembled into chains extending along [010] by O—H⋯N hydrogen bonds; adjacent chains are linked by O—H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For general background to coordination polymers, see: Bowers et al. (2005 ); Bowes et al. (2003 ). For related structures, see: Chen et al. (2005 ).

Experimental

Crystal data

C₁₀H₈N₂·C₉H₁₀O₈
M_r = 402.35
Orthorhombic, P n m a
a = 12.942 (3) Å
b = 25.118 (5) Å
c = 5.4353 (11) Å
V = 1766.8 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 293 K
0.44 × 0.36 × 0.27 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.949, T_max = 0.968
15967 measured reflections
2054 independent reflections
1499 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.089
S = 1.02
2054 reflections
141 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O3ⁱ	0.87 (2)	1.80 (2)	2.6520 (16)	165 (2)
O4—H4A⋯N1ⁱⁱ	0.94 (2)	1.80 (2)	2.7335 (18)	169 (2)
Symmetry codes: (i) $[x+{\script{1\over 2}}, y, -z-{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811025827/jh2304sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811025827/jh2304Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811025827/jh2304Isup3.cml

checkCIF report

Comment top

In hydrogen-bonded adducts of simple di–, tri– and tetracarboxylic acids with tertiary diamines, the modes of hydrogen-bonded chains are often determined by hard and soft types. Our investigation builds on the associative behavior of carboxyl and pyridine functions. In this contribution, we report the title compound with bipyridine–cyclopentanetetracarboxylic acid cocrystal.

The asymmetric unit contains one 2,2'-bipyridine molecule and one 1,2,3,4–cyclopentanetetracarboxylic acid molecule. Both bipyridine and cyclopentanetetracarboxylic acid molecules are generated via crystallographic 2–fold rotation axes (Fig. 1), and C3 atoms are located at the Wyckoff 4c sites. The carboxylic groups of cyclopentanetetracarboxylic acid connect with the corresponding bipyridine molecules through O4–H4A···N1ⁱⁱ hydrogen bonds generating a one-dimensional chain along [010] (Fig. 2). In this way, the adjacent one-dimensional chains are interconnected by O2–H2B···O3ⁱ hydrogen bonds to give three-dimensional network parallel to (001) (Fig. 3).

Related literature top

For general background [to what?], see: Bowers et al. (2005); Bowes et al. (2003). For related structures, see: Chen et al. (2005)

Experimental top

Under continuous stirring, a solution of 2,2'-bipyridine (0.1560 g, 1.00 mmol) in 10 ml CH₃OH was added dropwise to an aqueous solution of 1,2,3,4–cyclopentanetetracarboxylic acid (0.1230 g, 0.50 mmol) in 10 ml H₂O. The resulting mixture was further stirred for ca 30 min. After slow evaporation of the solution for one week at 35°C, colorless pillar sized crystals were obtained.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEP view of the title compound, The dispalcement ellipsoids are drawn at 45% probability dispalcement ellipsoids. [Symmetry codes: (i)x, –y+1/2, z;(ii)–x, y + 1, –z.]
	Fig. 2. one-dimensional chain of the title cocrystal viewed along the b axis. O–H···N hydrogen bonds are shown as dashed lines.
	Fig. 3. Packing diagram of the title co-crystal viewed down the c axis. O–H···N and O–H···O hydrogen bonds are shown as dashed lines.

2,2'-Bipyridine–cyclopentane-1,2,3,4-tetracarboxylic acid (1/1) top

Crystal data top

C₁₀H₈N₂·C₉H₁₀O₈	F(000) = 840
M_r = 402.35	D_x = 1.513 Mg m⁻³
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 8201 reflections
a = 12.942 (3) Å	θ = 3.2–27.5°
b = 25.118 (5) Å	µ = 0.12 mm⁻¹
c = 5.4353 (11) Å	T = 293 K
V = 1766.8 (6) Å³	Block, white
Z = 4	0.44 × 0.36 × 0.27 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2054 independent reflections
Radiation source: fine-focus sealed tube	1499 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
Detector resolution: 0 pixels mm^-1	θ_max = 27.4°, θ_min = 3.2°
ω scans	h = −16→16
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −32→32
T_min = 0.949, T_max = 0.968	l = −7→7
15967 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.034P)² + 0.4998P] where P = (F_o² + 2F_c²)/3
2054 reflections	(Δ/σ)_max = 0.001
141 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₀H₈N₂·C₉H₁₀O₈	V = 1766.8 (6) Å³
M_r = 402.35	Z = 4
Orthorhombic, Pnma	Mo Kα radiation
a = 12.942 (3) Å	µ = 0.12 mm⁻¹
b = 25.118 (5) Å	T = 293 K
c = 5.4353 (11) Å	0.44 × 0.36 × 0.27 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2054 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	1499 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.968	R_int = 0.055
15967 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.089	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.19 e Å⁻³
2054 reflections	Δρ_min = −0.16 e Å⁻³
141 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

	x	y	z	U_iso*/U_eq
C1	0.51833 (9)	0.28149 (5)	0.1032 (3)	0.0282 (3)
H1A	0.5337	0.2944	0.2694	0.034*
C2	0.40596 (10)	0.29744 (5)	0.0333 (3)	0.0311 (3)
H2A	0.3672	0.3004	0.1875	0.037*
C3	0.36186 (15)	0.2500	−0.1051 (4)	0.0354 (5)
H3A	0.3842	0.2500	−0.2754	0.043*
H3B	0.2869	0.2500	−0.0997	0.043*
O1	0.58022 (9)	0.31419 (5)	−0.2864 (2)	0.0560 (4)
O2	0.68873 (8)	0.30931 (4)	0.0286 (2)	0.0429 (3)
C4	0.59708 (10)	0.30368 (5)	−0.0745 (3)	0.0313 (3)
O3	0.33802 (8)	0.35651 (4)	−0.2754 (3)	0.0535 (4)
O4	0.44673 (9)	0.38926 (4)	0.0007 (2)	0.0438 (3)
C5	0.39410 (10)	0.34981 (6)	−0.0985 (3)	0.0341 (3)
N1	0.07695 (9)	0.51473 (5)	0.2707 (2)	0.0392 (3)
C6	0.14948 (12)	0.49161 (7)	0.4103 (3)	0.0456 (4)
H6A	0.1737	0.5103	0.5463	0.055*
C7	0.19052 (12)	0.44202 (7)	0.3654 (3)	0.0453 (4)
H7A	0.2406	0.4276	0.4683	0.054*
C8	0.15516 (13)	0.41452 (7)	0.1634 (3)	0.0448 (4)
H8A	0.1816	0.3811	0.1258	0.054*
C9	0.08006 (13)	0.43719 (6)	0.0176 (3)	0.0430 (4)
H9A	0.0553	0.4190	−0.1193	0.052*
C10	0.04132 (11)	0.48714 (6)	0.0747 (3)	0.0357 (3)
H2B	0.7334 (16)	0.3216 (8)	−0.077 (4)	0.074 (7)*
H4A	0.4380 (18)	0.4198 (10)	−0.098 (5)	0.095 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0233 (6)	0.0356 (7)	0.0258 (7)	−0.0014 (5)	0.0007 (6)	−0.0040 (6)
C2	0.0225 (6)	0.0321 (7)	0.0389 (8)	−0.0010 (5)	0.0033 (6)	−0.0016 (6)
C3	0.0260 (9)	0.0286 (10)	0.0517 (14)	0.000	−0.0046 (10)	0.000
O1	0.0469 (7)	0.0863 (10)	0.0350 (7)	−0.0119 (6)	0.0054 (5)	0.0090 (6)
O2	0.0249 (5)	0.0494 (7)	0.0544 (8)	−0.0087 (5)	0.0019 (5)	0.0014 (6)
C4	0.0279 (7)	0.0290 (7)	0.0371 (9)	−0.0010 (6)	0.0046 (6)	−0.0054 (6)
O3	0.0430 (6)	0.0380 (6)	0.0796 (9)	−0.0087 (5)	−0.0285 (6)	0.0102 (6)
O4	0.0467 (6)	0.0340 (6)	0.0508 (7)	−0.0104 (5)	−0.0073 (5)	−0.0026 (5)
C5	0.0236 (6)	0.0311 (7)	0.0475 (9)	−0.0015 (6)	0.0004 (7)	−0.0026 (7)
N1	0.0387 (7)	0.0378 (7)	0.0411 (8)	−0.0084 (6)	−0.0029 (6)	0.0029 (6)
C6	0.0430 (8)	0.0494 (9)	0.0443 (10)	−0.0126 (8)	−0.0101 (8)	0.0036 (8)
C7	0.0390 (8)	0.0458 (9)	0.0510 (11)	−0.0051 (7)	−0.0069 (8)	0.0125 (8)
C8	0.0467 (9)	0.0394 (9)	0.0483 (10)	−0.0018 (7)	0.0023 (8)	0.0083 (8)
C9	0.0507 (9)	0.0386 (8)	0.0396 (9)	−0.0046 (7)	−0.0054 (8)	0.0021 (7)
C10	0.0375 (7)	0.0353 (8)	0.0343 (8)	−0.0093 (6)	0.0013 (7)	0.0057 (7)

Geometric parameters (Å, º) top

C1—C4	1.5105 (19)	O4—C5	1.3177 (17)
C1—C2	1.5555 (18)	O4—H4A	0.94 (2)
C1—C1ⁱ	1.582 (3)	N1—C6	1.339 (2)
C1—H1A	0.9800	N1—C10	1.352 (2)
C2—C5	1.506 (2)	C6—C7	1.376 (2)
C2—C3	1.5202 (19)	C6—H6A	0.9300
C2—H2A	0.9800	C7—C8	1.375 (2)
C3—C2ⁱ	1.5202 (19)	C7—H7A	0.9300
C3—H3A	0.9700	C8—C9	1.377 (2)
C3—H3B	0.9700	C8—H8A	0.9300
O1—C4	1.2015 (19)	C9—C10	1.386 (2)
O2—C4	1.3194 (17)	C9—H9A	0.9300
O2—H2B	0.87 (2)	C10—C10ⁱⁱ	1.490 (3)
O3—C5	1.2166 (19)

C4—C1—C2	112.31 (12)	O2—C4—C1	111.99 (13)
C4—C1—C1ⁱ	111.65 (7)	C5—O4—H4A	108.6 (14)
C2—C1—C1ⁱ	104.92 (7)	O3—C5—O4	121.84 (14)
C4—C1—H1A	109.3	O3—C5—C2	123.90 (13)
C2—C1—H1A	109.3	O4—C5—C2	114.19 (13)
C1ⁱ—C1—H1A	109.3	C6—N1—C10	117.60 (14)
C5—C2—C3	114.28 (13)	N1—C6—C7	124.23 (16)
C5—C2—C1	115.88 (11)	N1—C6—H6A	117.9
C3—C2—C1	105.67 (12)	C7—C6—H6A	117.9
C5—C2—H2A	106.8	C8—C7—C6	117.89 (16)
C3—C2—H2A	106.8	C8—C7—H7A	121.1
C1—C2—H2A	106.8	C6—C7—H7A	121.1
C2—C3—C2ⁱ	103.21 (17)	C7—C8—C9	119.11 (16)
C2—C3—H3A	111.1	C7—C8—H8A	120.4
C2ⁱ—C3—H3A	111.1	C9—C8—H8A	120.4
C2—C3—H3B	111.1	C8—C9—C10	120.02 (16)
C2ⁱ—C3—H3B	111.1	C8—C9—H9A	120.0
H3A—C3—H3B	109.1	C10—C9—H9A	120.0
C4—O2—H2B	110.7 (14)	N1—C10—C9	121.14 (14)
O1—C4—O2	123.15 (14)	N1—C10—C10ⁱⁱ	116.88 (17)
O1—C4—C1	124.84 (13)	C9—C10—C10ⁱⁱ	121.98 (18)

Symmetry codes: (i) x, −y+1/2, z; (ii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3ⁱⁱⁱ	0.87 (2)	1.80 (2)	2.6520 (16)	165 (2)
O4—H4A···N1^iv	0.94 (2)	1.80 (2)	2.7335 (18)	169 (2)

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈N₂·C₉H₁₀O₈
M_r	402.35
Crystal system, space group	Orthorhombic, Pnma
Temperature (K)	293
a, b, c (Å)	12.942 (3), 25.118 (5), 5.4353 (11)
V (Å³)	1766.8 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.44 × 0.36 × 0.27

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.949, 0.968
No. of measured, independent and observed [I > 2σ(I)] reflections	15967, 2054, 1499
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.089, 1.02
No. of reflections	2054
No. of parameters	141
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O3ⁱ	0.87 (2)	1.80 (2)	2.6520 (16)	165 (2)
O4—H4A···N1ⁱⁱ	0.94 (2)	1.80 (2)	2.7335 (18)	169 (2)

Symmetry codes: (i) x+1/2, y, −z−1/2; (ii) −x+1/2, −y+1, z−1/2.

Acknowledgements

This project was supported by the Scientific Research Fund of Ningbo University (grant No. XKL069) and the Education Department of Zhejiang Province. Sincere thanks are also extended to the K. C. Wong Magna Fund in Ningbo University.

References

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