Butane-1,2,3,4-tetra­carboxylic acid–4,4′-bipyridine (1/2)

Zhang, N.; Shi, X.-M.; Shao, M.; Li, M.-X.

doi:10.1107/S1600536809029237

organic compounds

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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2016

doi:10.1107/S1600536809029237

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Butane-1,2,3,4-tetracarboxylic acid–4,4′-bipyridine (1/2)

Ning Zhang,^a Xue-Min Shi,^a Min Shao ^b and Ming-Xing Li ^a ^*

^aDepartment of Chemistry, College of Science, Shanghai University, Shanghai 200444, People's Republic of China, and ^bInstrumental Analysis and Research Center, Shanghai University, Shanghai 200444, People's Republic of China
^*Correspondence e-mail: mx_li@mail.shu.edu.cn

(Received 17 July 2009; accepted 23 July 2009; online 29 July 2009)

The hydrothermal reaction of butane-1,2,3,4-tetracarboxylic acid (H₄butca), 4,4′-bipyridine (bipy) and Mn(SO₄)₂·H₂O afforded a new co-crystal, C₈H₁₀O₈·2C₁₀H₈N₂ or H₄butca·2(bipy), in which strong O—H⋯N hydrogen-bonding and weak π–π stacking [centroid–centroid distance = 3.8459 (19) Å] interactions assemble the organic molecules into a three-dimensional supramolecular framework. C—H⋯O interactions are also present. The whole molecule has inversion symmetry.

Related literature

For the importance of hydrogen-bonding and π-π stacking interactions in supramolecular chemistry, crystal engineering and biological recognition, see: Wang et al. (2007 ). Many organic co-crystals have been assembled from N-heterocycles and polycarboxylic acids, see: Li et al. (2007 ). For the 1:1 co-crystal H₄butca·bipy, see: Najafpour et al. (2008 ).

Experimental

Crystal data

C₈H₁₀O₈·2C₁₀H₈N₂
M_r = 546.53
Triclinic, $[P \overline 1]$
a = 7.4435 (11) Å
b = 8.6990 (13) Å
c = 11.438 (2) Å
α = 99.819 (3)°
β = 105.662 (3)°
γ = 111.361 (2)°
V = 633.57 (17) Å³
Z = 1
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.30 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.969, T_max = 0.969
3287 measured reflections
2196 independent reflections
1721 reflections with I > 2σ(I)
R_int = 0.013

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.176
S = 1.07
2196 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.78 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O4	0.93	2.56	3.476 (3)	168
C9—H9⋯O2	0.93	2.51	3.425 (4)	167
O3—H3A⋯N1ⁱ	0.82	1.78	2.595 (3)	170
O2—H2⋯N2ⁱⁱ	0.82	1.84	2.642 (3)	167
Symmetry codes: (i) x+1, y+1, z; (ii) x-1, y-1, z-1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I, New_Global_Publ_Block. DOI: 10.1107/S1600536809029237/at2847sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029237/at2847Isup2.hkl

checkCIF report

Comment top

Organic cocrystals involving hydrogen-bonding (Table 1, Fig. 2) and π-π stacking [between the (N1/C5–C9) pyridine rings of 4,4'-bipyridine group, centroid-to-centroid distance = 3.8459 (19) Å] interactions are important in the areas of supramolecular chemistry, crystal engineering, and biological recognition (Wang et al., 2007). Many organic cocrystals have been assembled from N-heterocycle and polycarboxylic acids (Li et al., 2007). 4,4'-Bipyridine (bipy) and butane-1,2,3,4-tetracarboxylic acid (H₄butca) are important organic ligands in preparing metal complexes.

In our course of preparing ternary complexes containing butane-1,2,3,4-tetracarboxylic acid and 4,4'-bipyridine, a new 1:2 cocrystal compound of H₄butca.2bipy was prepared unexpectedly. Previously, a 1:1cocrystal of H₄butca.bipy has been synthesized by solution reaction (Najafpour, et al., 2008). Herein we report the supramolecular framework of the title compound (I) (Fig. 1). The whole molecule has an inversion symmetry which lies on the midpoint of the C3—C3Aa bond of the butane-1,2,3,4-tetracarboxylic acid moiety.

Related literature top

For the importance of hydrogen-bonding and π-π stacking interactions in supramolecular chemistry, crystal engineering and biological recognition, see: Wang et al. (2007). Many organic co-crystals have been assembled from N-heterocycles and polycarboxylic acids, see: Li et al. (2007). For the 1:1 co-crystal H₄butca.bipy, see: Najafpour et al. (2008).

Experimental top

A mixture of H₄butca (0.0468 g, 0.2 mmol), 4,4'-bipyridine (0.0468 g, 0.30 mmol), Mn(SO₄)₂.H₂O (0.0510 g, 0.3 mmol) and H₂O (10 ml) was sealed in a 15 ml Teflon-lined stainless-steel reactor, which was heated at 413 K for 72 h. The reaction mixture was cooled to room temperature at a rate of 10 K h^-1. Light yellow block crystals suitable for X-ray diffraction were obtained in 56% yield (0.0273 g, based on H₄butca). Analysis calculated for C₂₈H₂₆N₄O₈ (%): C 61.53, H 4.795, N 10.25. Found: C 61.16, H 4.622, N 10.23. IR (KBr pellet, cm^-1): 3093w, 3040w, 2921w, 1711 s, 1601 s, 1539m, 1498m, 1414 s,1396 s, 1365m, 1285 s, 1217 s, 1128 s, 1071 s, 1005 s, 882m, 816 s, 626 s, 534m.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of (I), showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. Crystal packing diagram of compound (I)

Butane-1,2,3,4-tetracarboxylic acid–4,4'-bipyridine (1/2) top

Crystal data top

C₈H₁₀O₈·2C₁₀H₈N₂	Z = 1
M_r = 546.53	F(000) = 286
Triclinic, P1	D_x = 1.432 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4435 (11) Å	Cell parameters from 1387 reflections
b = 8.6990 (13) Å	θ = 2.6–26.6°
c = 11.438 (2) Å	µ = 0.11 mm⁻¹
α = 99.819 (3)°	T = 296 K
β = 105.662 (3)°	Block, colourless
γ = 111.361 (2)°	0.30 × 0.30 × 0.30 mm
V = 633.57 (17) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2196 independent reflections
Radiation source: fine-focus sealed tube	1721 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.969, T_max = 0.969	k = −9→10
3287 measured reflections	l = −13→9

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.176	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0797P)² + 0.4629P] where P = (F_o² + 2F_c²)/3
2196 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.78 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₈H₁₀O₈·2C₁₀H₈N₂	γ = 111.361 (2)°
M_r = 546.53	V = 633.57 (17) Å³
Triclinic, P1	Z = 1
a = 7.4435 (11) Å	Mo Kα radiation
b = 8.6990 (13) Å	µ = 0.11 mm⁻¹
c = 11.438 (2) Å	T = 296 K
α = 99.819 (3)°	0.30 × 0.30 × 0.30 mm
β = 105.662 (3)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2196 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1721 reflections with I > 2σ(I)
T_min = 0.969, T_max = 0.969	R_int = 0.013
3287 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 1.07	Δρ_max = 0.78 e Å⁻³
2196 reflections	Δρ_min = −0.30 e Å⁻³
183 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	−0.1342 (5)	0.6302 (4)	−0.0696 (3)	0.0508 (7)
C2	−0.0232 (5)	0.7892 (4)	0.0456 (3)	0.0597 (9)
H2A	−0.1212	0.7939	0.0858	0.072*
H2B	0.0844	0.7742	0.1058	0.072*
C3	0.0728 (5)	0.9587 (3)	0.0242 (3)	0.0548 (8)
H3	0.1316	0.9400	−0.0410	0.066*
C4	0.2542 (5)	1.0895 (4)	0.1447 (3)	0.0498 (7)
C5	−0.2914 (4)	0.4885 (4)	0.4266 (3)	0.0479 (7)
H5	−0.3917	0.4111	0.4485	0.057*
C6	−0.1373 (4)	0.6347 (4)	0.5207 (3)	0.0449 (7)
H6	−0.1346	0.6548	0.6038	0.054*
C7	0.0146 (4)	0.7522 (3)	0.4900 (2)	0.0368 (6)
C8	−0.0007 (4)	0.7138 (4)	0.3640 (3)	0.0490 (7)
H8	0.0963	0.7888	0.3387	0.059*
C9	−0.1600 (5)	0.5644 (4)	0.2767 (3)	0.0543 (8)
H9	−0.1671	0.5408	0.1928	0.065*
C10	0.1856 (4)	0.9112 (3)	0.5876 (2)	0.0373 (6)
C11	0.2302 (4)	0.9316 (4)	0.7163 (3)	0.0467 (7)
H11	0.1531	0.8442	0.7436	0.056*
C12	0.3888 (4)	1.0814 (4)	0.8037 (3)	0.0515 (7)
H12	0.4160	1.0920	0.8897	0.062*
C13	0.4643 (4)	1.1920 (4)	0.6489 (3)	0.0500 (7)
H13	0.5455	1.2815	0.6249	0.060*
C14	0.3093 (4)	1.0477 (4)	0.5543 (3)	0.0452 (7)
H14	0.2869	1.0409	0.4692	0.054*
N1	−0.3041 (4)	0.4522 (3)	0.3059 (2)	0.0486 (6)
N2	0.5053 (3)	1.2116 (3)	0.7720 (2)	0.0480 (6)
O1	−0.1175 (4)	0.6219 (3)	−0.1724 (2)	0.0646 (6)
O2	−0.2488 (4)	0.5023 (3)	−0.0413 (2)	0.0675 (7)
H2	−0.3115	0.4168	−0.1043	0.101*
O3	0.4001 (3)	1.1949 (3)	0.11635 (17)	0.0535 (6)
H3A	0.4895	1.2695	0.1816	0.080*
O4	0.2601 (3)	1.0897 (3)	0.25184 (19)	0.0617 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0491 (16)	0.0413 (16)	0.0448 (17)	0.0165 (13)	0.0013 (13)	0.0039 (13)
C2	0.0589 (19)	0.0442 (17)	0.0560 (19)	0.0128 (15)	0.0062 (15)	0.0121 (14)
C3	0.0543 (17)	0.0355 (15)	0.0479 (17)	0.0079 (13)	−0.0013 (14)	0.0065 (12)
C4	0.0508 (17)	0.0385 (15)	0.0391 (16)	0.0143 (13)	−0.0039 (13)	0.0051 (12)
C5	0.0422 (15)	0.0415 (15)	0.0449 (16)	0.0070 (13)	0.0106 (12)	0.0105 (12)
C6	0.0477 (15)	0.0451 (15)	0.0353 (14)	0.0143 (13)	0.0142 (12)	0.0103 (12)
C7	0.0358 (13)	0.0365 (13)	0.0354 (13)	0.0156 (11)	0.0095 (11)	0.0098 (11)
C8	0.0465 (16)	0.0501 (16)	0.0375 (15)	0.0092 (13)	0.0148 (12)	0.0096 (12)
C9	0.0551 (17)	0.0537 (17)	0.0353 (15)	0.0106 (14)	0.0126 (13)	0.0038 (13)
C10	0.0348 (13)	0.0363 (13)	0.0370 (14)	0.0146 (11)	0.0102 (11)	0.0079 (11)
C11	0.0471 (15)	0.0432 (15)	0.0377 (14)	0.0086 (13)	0.0138 (12)	0.0100 (12)
C12	0.0498 (16)	0.0526 (17)	0.0360 (15)	0.0120 (14)	0.0100 (13)	0.0068 (13)
C13	0.0447 (16)	0.0410 (15)	0.0536 (17)	0.0087 (13)	0.0148 (13)	0.0159 (13)
C14	0.0453 (15)	0.0460 (15)	0.0395 (15)	0.0142 (13)	0.0145 (12)	0.0150 (12)
N1	0.0450 (13)	0.0419 (13)	0.0417 (14)	0.0105 (11)	0.0060 (10)	0.0056 (10)
N2	0.0398 (12)	0.0424 (13)	0.0469 (14)	0.0088 (10)	0.0098 (10)	0.0079 (10)
O1	0.0678 (15)	0.0481 (13)	0.0711 (16)	0.0150 (11)	0.0286 (12)	0.0185 (11)
O2	0.0788 (16)	0.0500 (13)	0.0436 (12)	0.0084 (12)	0.0114 (11)	0.0034 (10)
O3	0.0456 (11)	0.0456 (12)	0.0373 (11)	0.0028 (9)	−0.0005 (9)	−0.0005 (9)
O4	0.0599 (13)	0.0513 (13)	0.0424 (12)	0.0047 (10)	0.0019 (10)	0.0097 (9)

Geometric parameters (Å, º) top

C1—O1	1.209 (4)	C7—C10	1.484 (4)
C1—O2	1.285 (4)	C8—C9	1.374 (4)
C1—C2	1.513 (4)	C8—H8	0.9300
C2—C3	1.482 (4)	C9—N1	1.325 (4)
C2—H2A	0.9700	C9—H9	0.9300
C2—H2B	0.9700	C10—C11	1.383 (4)
C3—C4	1.536 (4)	C10—C14	1.395 (4)
C3—C3ⁱ	1.542 (6)	C11—C12	1.374 (4)
C3—H3	0.9800	C11—H11	0.9300
C4—O4	1.214 (3)	C12—N2	1.327 (4)
C4—O3	1.301 (4)	C12—H12	0.9300
C5—N1	1.332 (4)	C13—N2	1.324 (4)
C5—C6	1.377 (4)	C13—C14	1.373 (4)
C5—H5	0.9300	C13—H13	0.9300
C6—C7	1.393 (4)	C14—H14	0.9300
C6—H6	0.9300	O2—H2	0.8200
C7—C8	1.386 (4)	O3—H3A	0.8200

O1—C1—O2	124.5 (3)	C6—C7—C10	121.7 (2)
O1—C1—C2	126.0 (3)	C9—C8—C7	119.6 (3)
O2—C1—C2	109.5 (3)	C9—C8—H8	120.2
C3—C2—C1	117.3 (3)	C7—C8—H8	120.2
C3—C2—H2A	108.0	N1—C9—C8	123.5 (3)
C1—C2—H2A	108.0	N1—C9—H9	118.3
C3—C2—H2B	108.0	C8—C9—H9	118.3
C1—C2—H2B	108.0	C11—C10—C14	116.6 (2)
H2A—C2—H2B	107.2	C11—C10—C7	121.5 (2)
C2—C3—C4	110.8 (2)	C14—C10—C7	121.8 (2)
C2—C3—C3ⁱ	116.5 (3)	C12—C11—C10	119.8 (3)
C4—C3—C3ⁱ	108.9 (3)	C12—C11—H11	120.1
C2—C3—H3	106.7	C10—C11—H11	120.1
C4—C3—H3	106.7	N2—C12—C11	123.5 (3)
C3ⁱ—C3—H3	106.7	N2—C12—H12	118.2
O4—C4—O3	125.2 (2)	C11—C12—H12	118.2
O4—C4—C3	123.6 (3)	N2—C13—C14	124.0 (3)
O3—C4—C3	111.2 (3)	N2—C13—H13	118.0
N1—C5—C6	123.4 (3)	C14—C13—H13	118.0
N1—C5—H5	118.3	C13—C14—C10	119.2 (3)
C6—C5—H5	118.3	C13—C14—H14	120.4
C5—C6—C7	119.2 (2)	C10—C14—H14	120.4
C5—C6—H6	120.4	C9—N1—C5	117.3 (2)
C7—C6—H6	120.4	C13—N2—C12	116.9 (2)
C8—C7—C6	117.0 (2)	C1—O2—H2	109.5
C8—C7—C10	121.3 (2)	C4—O3—H3A	109.5

Symmetry code: (i) −x, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O4	0.93	2.56	3.476 (3)	168
C9—H9···O2	0.93	2.51	3.425 (4)	167
O3—H3A···N1ⁱⁱ	0.82	1.78	2.595 (3)	170
O2—H2···N2ⁱⁱⁱ	0.82	1.84	2.642 (3)	167

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀O₈·2C₁₀H₈N₂
M_r	546.53
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	7.4435 (11), 8.6990 (13), 11.438 (2)
α, β, γ (°)	99.819 (3), 105.662 (3), 111.361 (2)
V (Å³)	633.57 (17)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.969, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	3287, 2196, 1721
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.176, 1.07
No. of reflections	2196
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.78, −0.30

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), 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
C14—H14···O4	0.93	2.56	3.476 (3)	168.3
C9—H9···O2	0.93	2.51	3.425 (4)	166.8
O3—H3A···N1ⁱ	0.82	1.78	2.595 (3)	170.4
O2—H2···N2ⁱⁱ	0.82	1.84	2.642 (3)	167.1

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

Acknowledgements

The project was supported by the Leading Academic Discipline Project of Shanghai Municipal Education Commission (J50102), China.

References

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