4,4'-Bipyridine-cyclo-hexane-1,2,4,5-tetra-carb-oxy-lic acid (1/1).

In the title 1:1 adduct, C(10)H(8)N(2)·C(10)H(12)O(8), the dihedral angle between the pyridine rings in the 4,4-bipyridine molecule is 8.33 (13)°. In the crystal, the cyclo-hexane-1,2,4,5-tetra-carb-oxy-lic acid mol-ecules inter-act with each other through inter-molecular O-H⋯O hydrogen bonds, forming an infinite chain along the a axis, which is further linked perpendicularly by O-H⋯N hydrogen bonds involving bipyridine, resulting in a supra-molecular corrugated sheet parallel to the (110) plane.

Related literature

For background to crystal engineering, see: Desiraju (1989 ▶); Schultheiss et al. (2010 ▶); Ebenezer & Muthiah (2010 ▶); An et al. (2010 ▶). For a related flexible tetracarboxylic acid, see Holmes et al. (1987 ▶); Wang et al. (2009 ▶). For a related structure, see: Bhogala et al.(2005 ▶).

Experimental

Crystal data

C10H8N2·C10H12O8

M = 416.38

Monoclinic,

a = 12.345 (3) Å

b = 9.724 (2) Å

c = 16.497 (4) Å

β = 106.364 (3)°

V = 1900.1 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.22 × 0.15 × 0.08 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2008 ▶) T min = 0.975, T max = 0.991

9330 measured reflections

3416 independent reflections

2243 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.143

S = 1.05

3416 reflections

275 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039024/dn2606sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039024/dn2606Isup2.hkl

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

C10H8N2·C10H12O8	F(000) = 872
Mr = 416.38	Dx = 1.456 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3417 reflections
a = 12.345 (3) Å	θ = 1.7–25.2°
b = 9.724 (2) Å	µ = 0.11 mm−1
c = 16.497 (4) Å	T = 298 K
β = 106.364 (3)°	Block, colourless
V = 1900.1 (8) Å3	0.22 × 0.15 × 0.08 mm
Z = 4

Bruker APEXII area-detector diffractometer	3416 independent reflections
Radiation source: fine-focus sealed tube	2243 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scan	θmax = 25.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −14→14
Tmin = 0.975, Tmax = 0.991	k = −11→11
9330 measured reflections	l = −19→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0639P)2 + 0.4389P] where P = (Fo2 + 2Fc2)/3
3416 reflections	(Δ/σ)max < 0.001
275 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.27706 (14)	0.44090 (19)	0.44732 (12)	0.0641 (5)
H1	0.2994	0.5168	0.4665	0.096*
O2	0.11097 (14)	0.54658 (17)	0.41482 (10)	0.0518 (5)
O3	0.18983 (14)	0.55768 (18)	0.23240 (12)	0.0636 (5)
O4	0.34420 (14)	0.42876 (17)	0.26978 (12)	0.0589 (5)
H4	0.3756	0.5037	0.2794	0.088*
O5	−0.04992 (17)	0.3310 (2)	0.45621 (11)	0.0667 (5)
H5	−0.0883	0.3681	0.4832	0.100*
O6	−0.15670 (16)	0.4586 (2)	0.35120 (11)	0.0692 (6)
O7	−0.05944 (14)	0.47589 (18)	0.07724 (9)	0.0553 (5)
O8	0.10445 (14)	0.3927 (2)	0.06854 (10)	0.0578 (5)
H8	0.0852	0.4324	0.0229	0.087*
C11	0.0262 (2)	0.4068 (2)	0.10675 (14)	0.0448 (6)
C12	0.04494 (19)	0.3292 (2)	0.18872 (13)	0.0434 (6)
H12	0.0147	0.2365	0.1738	0.052*
C13	−0.02428 (18)	0.3930 (2)	0.24293 (13)	0.0439 (6)
H13A	−0.0030	0.4887	0.2537	0.053*
H13B	−0.1037	0.3900	0.2120	0.053*
C14	−0.00665 (19)	0.3186 (2)	0.32665 (14)	0.0447 (6)
H14	−0.0332	0.2241	0.3130	0.054*
C15	−0.0792 (2)	0.3797 (3)	0.37755 (15)	0.0510 (6)
C16	0.11869 (19)	0.3086 (2)	0.37600 (14)	0.0439 (6)
H16	0.1234	0.2463	0.4236	0.053*
C17	0.1676 (2)	0.4448 (3)	0.41336 (13)	0.0448 (6)
C18	0.1851 (2)	0.2407 (2)	0.32092 (14)	0.0462 (6)
H18A	0.1610	0.1457	0.3110	0.055*
H18B	0.2646	0.2405	0.3517	0.055*
C19	0.17057 (19)	0.3116 (2)	0.23536 (14)	0.0426 (6)
H19	0.2032	0.2509	0.2011	0.051*
C20	0.23417 (19)	0.4466 (2)	0.24532 (13)	0.0434 (6)
N1	0.64426 (18)	1.3190 (2)	0.48929 (14)	0.0598 (6)
N2	0.45114 (19)	0.6692 (2)	0.31157 (14)	0.0628 (6)
C1	0.3891 (2)	0.7823 (3)	0.2905 (2)	0.0752 (9)
H1A	0.3180	0.7743	0.2521	0.090*
C2	0.5531 (2)	0.6854 (3)	0.36420 (18)	0.0708 (8)
H2	0.5992	0.6083	0.3784	0.085*
C3	0.5951 (2)	0.8100 (3)	0.39928 (17)	0.0642 (8)
H3	0.6675	0.8154	0.4360	0.077*
C4	0.4243 (2)	0.9105 (3)	0.32249 (19)	0.0713 (8)
H4A	0.3774	0.9863	0.3056	0.086*
C5	0.5293 (2)	0.9264 (3)	0.37970 (15)	0.0502 (6)
C6	0.5699 (2)	1.0628 (3)	0.41730 (15)	0.0510 (6)
C7	0.6679 (2)	1.0774 (3)	0.4825 (2)	0.0817 (10)
H7	0.7114	1.0005	0.5039	0.098*
C8	0.7015 (2)	1.2050 (3)	0.5157 (2)	0.0809 (10)
H8A	0.7682	1.2116	0.5592	0.097*
C9	0.5115 (2)	1.1812 (3)	0.39072 (19)	0.0710 (8)
H9	0.4452	1.1782	0.3466	0.085*
C10	0.5494 (2)	1.3050 (3)	0.42825 (19)	0.0770 (9)
H10	0.5059	1.3829	0.4096	0.092*

	U11	U22	U33	U12	U13	U23
O1	0.0506 (10)	0.0539 (12)	0.0736 (12)	0.0025 (9)	−0.0055 (9)	−0.0150 (9)
O2	0.0551 (10)	0.0423 (10)	0.0511 (10)	0.0043 (8)	0.0035 (8)	−0.0037 (7)
O3	0.0496 (10)	0.0378 (11)	0.0928 (14)	−0.0003 (8)	0.0027 (9)	0.0034 (9)
O4	0.0451 (10)	0.0509 (11)	0.0739 (12)	−0.0023 (8)	0.0055 (9)	−0.0018 (9)
O5	0.0850 (14)	0.0675 (13)	0.0526 (11)	0.0182 (10)	0.0275 (10)	0.0121 (9)
O6	0.0627 (12)	0.0789 (14)	0.0641 (12)	0.0200 (11)	0.0148 (9)	0.0068 (10)
O7	0.0520 (10)	0.0667 (12)	0.0430 (9)	0.0097 (9)	0.0066 (8)	0.0042 (8)
O8	0.0573 (11)	0.0720 (13)	0.0431 (10)	0.0095 (9)	0.0123 (8)	0.0055 (8)
C11	0.0442 (14)	0.0421 (14)	0.0432 (13)	−0.0045 (11)	0.0042 (11)	−0.0098 (10)
C12	0.0472 (13)	0.0361 (13)	0.0405 (12)	−0.0070 (10)	0.0019 (10)	−0.0041 (10)
C13	0.0406 (13)	0.0433 (14)	0.0429 (12)	−0.0008 (11)	0.0040 (10)	0.0006 (10)
C14	0.0496 (13)	0.0344 (13)	0.0472 (13)	−0.0021 (11)	0.0090 (11)	−0.0006 (10)
C15	0.0538 (15)	0.0488 (16)	0.0481 (14)	−0.0035 (13)	0.0106 (12)	0.0012 (12)
C16	0.0499 (14)	0.0350 (13)	0.0435 (13)	0.0012 (11)	0.0079 (10)	0.0055 (10)
C17	0.0506 (15)	0.0448 (15)	0.0341 (12)	0.0025 (12)	0.0038 (10)	0.0021 (10)
C18	0.0528 (14)	0.0309 (13)	0.0500 (13)	0.0029 (11)	0.0064 (11)	0.0011 (10)
C19	0.0460 (13)	0.0346 (13)	0.0447 (13)	0.0006 (10)	0.0085 (10)	−0.0041 (10)
C20	0.0417 (13)	0.0461 (15)	0.0377 (12)	−0.0015 (11)	0.0037 (10)	−0.0014 (10)
N1	0.0532 (13)	0.0507 (14)	0.0681 (14)	−0.0042 (11)	0.0051 (11)	−0.0076 (11)
N2	0.0562 (14)	0.0545 (15)	0.0725 (15)	−0.0120 (12)	0.0098 (12)	−0.0052 (11)
C1	0.0527 (17)	0.064 (2)	0.097 (2)	−0.0059 (15)	0.0005 (15)	−0.0144 (17)
C2	0.0712 (19)	0.0468 (17)	0.081 (2)	−0.0035 (14)	0.0001 (16)	0.0061 (14)
C3	0.0571 (16)	0.0519 (17)	0.0703 (18)	−0.0051 (13)	−0.0037 (13)	0.0025 (13)
C4	0.0489 (16)	0.0555 (18)	0.096 (2)	−0.0009 (13)	−0.0007 (15)	−0.0136 (15)
C5	0.0472 (14)	0.0479 (16)	0.0551 (14)	−0.0075 (12)	0.0140 (11)	−0.0017 (11)
C6	0.0438 (14)	0.0524 (16)	0.0554 (15)	−0.0050 (12)	0.0116 (11)	−0.0009 (12)
C7	0.0556 (17)	0.0535 (19)	0.113 (3)	0.0029 (14)	−0.0137 (17)	−0.0099 (17)
C8	0.0566 (18)	0.063 (2)	0.100 (2)	−0.0029 (16)	−0.0161 (16)	−0.0139 (17)
C9	0.0581 (17)	0.0552 (18)	0.0795 (19)	−0.0018 (14)	−0.0135 (14)	−0.0039 (14)
C10	0.0664 (19)	0.0549 (19)	0.090 (2)	0.0023 (15)	−0.0099 (16)	−0.0040 (15)

O1—C17	1.310 (3)	C18—H18A	0.9700
O1—H1	0.8200	C18—H18B	0.9700
O2—C17	1.215 (3)	C19—C20	1.515 (3)
O3—C20	1.202 (3)	C19—H19	0.9800
O4—C20	1.315 (3)	N1—C10	1.319 (3)
O4—H4	0.8200	N1—C8	1.321 (3)
O5—C15	1.332 (3)	N2—C2	1.321 (3)
O5—H5	0.8200	N2—C1	1.329 (4)
O6—C15	1.207 (3)	C1—C4	1.375 (4)
O7—C11	1.231 (3)	C1—H1A	0.9300
O8—C11	1.301 (3)	C2—C3	1.379 (4)
O8—H8	0.8200	C2—H2	0.9300
C11—C12	1.508 (3)	C3—C5	1.378 (4)
C12—C13	1.532 (3)	C3—H3	0.9300
C12—C19	1.534 (3)	C4—C5	1.380 (3)
C12—H12	0.9800	C4—H4A	0.9300
C13—C14	1.520 (3)	C5—C6	1.490 (3)
C13—H13A	0.9700	C6—C9	1.364 (4)
C13—H13B	0.9700	C6—C7	1.381 (4)
C14—C15	1.512 (3)	C7—C8	1.372 (4)
C14—C16	1.535 (3)	C7—H7	0.9300
C14—H14	0.9800	C8—H8A	0.9300
C16—C17	1.513 (3)	C9—C10	1.374 (4)
C16—C18	1.534 (3)	C9—H9	0.9300
C16—H16	0.9800	C10—H10	0.9300
C18—C19	1.535 (3)
C17—O1—H1	109.5	H18A—C18—H18B	107.6
C20—O4—H4	109.5	C20—C19—C12	112.18 (19)
C15—O5—H5	109.5	C20—C19—C18	111.54 (18)
C11—O8—H8	109.5	C12—C19—C18	110.52 (19)
O7—C11—O8	122.5 (2)	C20—C19—H19	107.5
O7—C11—C12	121.7 (2)	C12—C19—H19	107.5
O8—C11—C12	115.7 (2)	C18—C19—H19	107.5
C11—C12—C13	110.54 (19)	O3—C20—O4	123.5 (2)
C11—C12—C19	112.56 (19)	O3—C20—C19	124.3 (2)
C13—C12—C19	113.81 (18)	O4—C20—C19	112.2 (2)
C11—C12—H12	106.5	C10—N1—C8	116.2 (2)
C13—C12—H12	106.5	C2—N2—C1	116.4 (2)
C19—C12—H12	106.5	N2—C1—C4	123.6 (3)
C14—C13—C12	112.17 (19)	N2—C1—H1A	118.2
C14—C13—H13A	109.2	C4—C1—H1A	118.2
C12—C13—H13A	109.2	N2—C2—C3	123.8 (3)
C14—C13—H13B	109.2	N2—C2—H2	118.1
C12—C13—H13B	109.2	C3—C2—H2	118.1
H13A—C13—H13B	107.9	C5—C3—C2	119.8 (2)
C15—C14—C13	111.2 (2)	C5—C3—H3	120.1
C15—C14—C16	113.39 (19)	C2—C3—H3	120.1
C13—C14—C16	112.16 (19)	C1—C4—C5	119.9 (3)
C15—C14—H14	106.5	C1—C4—H4A	120.1
C13—C14—H14	106.5	C5—C4—H4A	120.1
C16—C14—H14	106.5	C3—C5—C4	116.5 (2)
O6—C15—O5	123.2 (2)	C3—C5—C6	121.8 (2)
O6—C15—C14	125.7 (2)	C4—C5—C6	121.7 (2)
O5—C15—C14	111.1 (2)	C9—C6—C7	115.6 (2)
C17—C16—C18	113.58 (19)	C9—C6—C5	122.2 (2)
C17—C16—C14	112.76 (19)	C7—C6—C5	122.3 (2)
C18—C16—C14	109.87 (18)	C8—C7—C6	120.2 (3)
C17—C16—H16	106.7	C8—C7—H7	119.9
C18—C16—H16	106.7	C6—C7—H7	119.9
C14—C16—H16	106.7	N1—C8—C7	123.7 (3)
O2—C17—O1	123.0 (2)	N1—C8—H8A	118.2
O2—C17—C16	123.7 (2)	C7—C8—H8A	118.2
O1—C17—C16	113.2 (2)	C6—C9—C10	120.9 (2)
C16—C18—C19	114.08 (18)	C6—C9—H9	119.6
C16—C18—H18A	108.7	C10—C9—H9	119.6
C19—C18—H18A	108.7	N1—C10—C9	123.4 (3)
C16—C18—H18B	108.7	N1—C10—H10	118.3
C19—C18—H18B	108.7	C9—C10—H10	118.3

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.82	1.81	2.630 (3)	177
O4—H4···N2	0.82	1.86	2.678 (3)	175
O5—H5···O2ii	0.82	1.96	2.723 (2)	153
O8—H8···O7iii	0.82	1.82	2.641 (2)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.82	1.81	2.630 (3)	177
O4—H4⋯N2	0.82	1.86	2.678 (3)	175
O5—H5⋯O2ii	0.82	1.96	2.723 (2)	153
O8—H8⋯O7iii	0.82	1.82	2.641 (2)	174

Symmetry codes: (i) ; (ii) ; (iii) .