2,2'-Bipyridine-cyclo-pentane-1,2,3,4-tetra-carb-oxy-lic acid (1/1).

The asymmetric unit of the title compound, C(10)H(8)N(2)·C(9)H(10)O(8), 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 mol-ecules 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 = 402.35

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.089

S = 1.02

2054 reflections

141 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811025827/jh2304sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811025827/jh2304Isup3.cml

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

C10H8N2·C9H10O8	F(000) = 840
Mr = 402.35	Dx = 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

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

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(Fo2) + (0.034P)2 + 0.4998P] where P = (Fo2 + 2Fc2)/3
2054 reflections	(Δ/σ)max = 0.001
141 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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···N1iv	0.94 (2)	1.80 (2)	2.7335 (18)	169 (2)

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) ; (ii) .