Butane-1,2,3,4-tetra­carboxylic acid dihydrate

Cheng, Y.; Wu, J.; Zhu, H.-L.; Lin, J.

doi:10.1107/S1600536809009970

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o835

doi:10.1107/S1600536809009970

Open

access

Butane-1,2,3,4-tetracarboxylic acid dihydrate

Yu Cheng,^a Jiang Wu,^a Hong-Lin Zhu ^a and Jian-li Lin ^a ^*

^aState Key Laboratory Base of Novel Functional Materials and Preparation Science, Faculty of Materials Science and Chemical Engineering, Institute of Solid Materials Chemistry, Ningbo University, Zhejiang 315211, People's Republic of China
^*Correspondence e-mail: zhengyueqing@nbu.edu.cn

(Received 5 March 2009; accepted 18 March 2009; online 25 March 2009)

The asymmetric unit of the title compound, C₈H₁₀O₈·2H₂O, contains one half-molecule of butane-1,2,3,4-tetracarboxylic acid and a water molecule, with the complete tetra-acid generated by crystallographic inversion symmetry. Intermolecular O—H⋯O hydrogen bonds form an extensive three-dimensional network, which consolidates the crystal packing.

Related literature

For applications of butane-1,2,3,4-tetracarboxylic acid in metal -organic coordination polymers, see: Delgado et al. (2007 ); Liu et al. (2008 ). For related crystal structures, see: McKee et al. (2007 ); Najafpour et al. (2008 ).

Experimental

Crystal data

C₈H₁₀O₈·2H₂O
M_r = 270.19
Monoclinic, P 2₁ /c
a = 7.4668 (15) Å
b = 9.3385 (19) Å
c = 8.8406 (18) Å
β = 109.60 (3)°
V = 580.7 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 293 K
0.55 × 0.46 × 0.26 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.921, T_max = 0.965
5478 measured reflections
1327 independent reflections
960 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.17
1327 reflections
82 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2C⋯O5ⁱ	0.85	1.87	2.707 (2)	167
O4—H4A⋯O5ⁱⁱ	0.86	1.83	2.689 (2)	178
O5—H5A⋯O3	0.83	1.93	2.754 (2)	172
O5—H5B⋯O1ⁱⁱⁱ	0.81	2.01	2.814 (2)	170
Symmetry codes: (i) x-1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536809009970/cv2528sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009970/cv2528Isup2.hkl

checkCIF report

Comment top

A search of the Cambridge Structural Database (Version 5.30, February 2009) showed that most of literature dealing with butane-1,2,3,4-tetracarboxylic acid mainly concentrated in the metal organic coordination polymers (Delgado et al., 2007; Liu et al., 2008). In this paper, we report the crystal structure of butane–1,2,3,4–tetracarboxylic acid dihydrate (Fig. 1).

The asymmetric unit of the title compound contains a half of the butane-1,2,3,4-tetracarboxylic acid molecule and one water molecule. The carboxylic acid group with C1 and C4 atoms are gauche with the C1—C2—C3—C4 torsion angle being 62.13 (1)°, which match well with that in the reported structures (McKee et al., 2007; Najafpour et al., 2008). Intermolecular O—H···O hydrogen bonds (Table 1) form an extensive three-dimensional hydrogen-bonding network, which consolidate the crystal packing.

Related literature top

For applications of butane-1,2,3,4-tetracarboxylic acid in metal -organic coordination polymers, see: Delgado et al. (2007); Liu et al. (2008). For related crystal structures, see: McKee et al. (2007); Najafpour et al. (2008).

Experimental top

Zn(NO₃)₂.6H₂O (0.1461 g, 1.0 mmol) was added to a stirred aqueous solution of butane-1,2,3,4-tetracarboxylic acid (0.1176 g, 0.50 mmol) in 15 ml H₂O, the resulting mixture was stirred for 20 min and then was filtered out. Colorless crystals were obtained from the filtrate (pH=2.80) after standing at room temperature for three months.

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. View of the title compound showing the atomic numbering and 45% probability dispalcement ellipsoids [symmetry code: (i) -x + 1, -y + 1, -z]. H atoms omitted for clarity.

Butane-1,2,3,4-tetracarboxylic acid dihydrate top

Crystal data top

C₈H₁₀O₈·2H₂O	F(000) = 284
M_r = 270.19	D_x = 1.545 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5478 reflections
a = 7.4668 (15) Å	θ = 3.3–27.4°
b = 9.3385 (19) Å	µ = 0.15 mm⁻¹
c = 8.8406 (18) Å	T = 293 K
β = 109.60 (3)°	Platelet, colorless
V = 580.7 (2) Å³	0.55 × 0.46 × 0.26 mm
Z = 2

Data collection top

Rigaku R-AXIS RAPID diffractometer	1327 independent reflections
Radiation source: fine-focus sealed tube	960 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 0 pixels mm^-1	θ_max = 27.4°, θ_min = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −12→12
T_min = 0.921, T_max = 0.965	l = −11→11
5478 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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0345P)² + 0.3695P] where P = (F_o² + 2F_c²)/3
1327 reflections	(Δ/σ)_max < 0.001
82 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₈H₁₀O₈·2H₂O	V = 580.7 (2) Å³
M_r = 270.19	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.4668 (15) Å	µ = 0.15 mm⁻¹
b = 9.3385 (19) Å	T = 293 K
c = 8.8406 (18) Å	0.55 × 0.46 × 0.26 mm
β = 109.60 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	1327 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	960 reflections with I > 2σ(I)
T_min = 0.921, T_max = 0.965	R_int = 0.027
5478 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.17	Δρ_max = 0.26 e Å⁻³
1327 reflections	Δρ_min = −0.23 e Å⁻³
82 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
O1	0.1296 (3)	0.38628 (19)	0.1509 (2)	0.0561 (5)
O2	0.0636 (2)	0.20225 (18)	−0.0167 (2)	0.0494 (5)
H2C	−0.0132	0.1808	0.0327	0.074*
C1	0.1546 (3)	0.3207 (2)	0.0422 (2)	0.0319 (5)
C2	0.2916 (3)	0.3636 (2)	−0.0416 (2)	0.0371 (5)
H2A	0.2201	0.3991	−0.1479	0.044*
H2B	0.3613	0.2795	−0.0547	0.044*
C3	0.4336 (3)	0.4784 (2)	0.0479 (2)	0.0294 (4)
H3A	0.3640	0.5630	0.0633	0.035*
C4	0.5554 (3)	0.4210 (2)	0.2107 (2)	0.0299 (4)
O3	0.6322 (3)	0.30568 (17)	0.23027 (19)	0.0510 (5)
O4	0.5724 (2)	0.50976 (17)	0.33017 (16)	0.0454 (4)
H4A	0.6470	0.4737	0.4186	0.068*
O5	0.8064 (2)	0.09678 (15)	0.10900 (16)	0.0369 (4)
H5A	0.7639	0.1616	0.1518	0.055*
H5B	0.8321	0.0309	0.1725	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0693 (12)	0.0600 (11)	0.0536 (10)	−0.0267 (9)	0.0398 (9)	−0.0219 (8)
O2	0.0483 (9)	0.0517 (10)	0.0578 (10)	−0.0243 (8)	0.0303 (8)	−0.0182 (8)
C1	0.0289 (10)	0.0377 (11)	0.0272 (9)	−0.0048 (8)	0.0069 (8)	0.0003 (8)
C2	0.0337 (10)	0.0477 (13)	0.0309 (10)	−0.0117 (9)	0.0124 (8)	−0.0073 (9)
C3	0.0267 (9)	0.0347 (11)	0.0286 (9)	−0.0025 (8)	0.0116 (8)	−0.0012 (8)
C4	0.0275 (9)	0.0348 (11)	0.0294 (9)	−0.0040 (8)	0.0122 (8)	−0.0023 (8)
O3	0.0669 (11)	0.0366 (9)	0.0451 (9)	0.0151 (8)	0.0126 (8)	−0.0019 (7)
O4	0.0549 (10)	0.0470 (9)	0.0278 (7)	0.0170 (7)	0.0054 (7)	−0.0057 (6)
O5	0.0434 (8)	0.0352 (8)	0.0358 (7)	−0.0005 (6)	0.0182 (6)	0.0018 (6)

Geometric parameters (Å, º) top

O1—C1	1.206 (2)	C3—C3ⁱ	1.559 (3)
O2—C1	1.311 (2)	C3—H3A	0.9800
O2—H2C	0.8523	C4—O3	1.205 (2)
C1—C2	1.505 (3)	C4—O4	1.315 (2)
C2—C3	1.528 (3)	O4—H4A	0.8618
C2—H2A	0.9700	O5—H5A	0.8314
C2—H2B	0.9700	O5—H5B	0.8111
C3—C4	1.518 (3)

C1—O2—H2C	110.1	C4—C3—C3ⁱ	108.55 (18)
O1—C1—O2	123.13 (18)	C2—C3—C3ⁱ	110.94 (19)
O1—C1—C2	124.71 (18)	C4—C3—H3A	109.3
O2—C1—C2	112.15 (17)	C2—C3—H3A	109.3
C1—C2—C3	113.57 (16)	C3ⁱ—C3—H3A	109.3
C1—C2—H2A	108.9	O3—C4—O4	122.30 (18)
C3—C2—H2A	108.9	O3—C4—C3	123.80 (18)
C1—C2—H2B	108.9	O4—C4—C3	113.89 (17)
C3—C2—H2B	108.9	C4—O4—H4A	110.0
H2A—C2—H2B	107.7	H5A—O5—H5B	105.9
C4—C3—C2	109.54 (16)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2C···O5ⁱⁱ	0.85	1.87	2.707 (2)	167
O4—H4A···O5ⁱⁱⁱ	0.86	1.83	2.689 (2)	178
O5—H5A···O3	0.83	1.93	2.754 (2)	172
O5—H5B···O1^iv	0.81	2.01	2.814 (2)	170

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

Experimental details

Crystal data
Chemical formula	C₈H₁₀O₈·2H₂O
M_r	270.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.4668 (15), 9.3385 (19), 8.8406 (18)
β (°)	109.60 (3)
V (Å³)	580.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.55 × 0.46 × 0.26

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.921, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	5478, 1327, 960
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.647

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.17
No. of reflections	1327
No. of parameters	82
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

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—H2C···O5ⁱ	0.85	1.87	2.707 (2)	167
O4—H4A···O5ⁱⁱ	0.86	1.83	2.689 (2)	178
O5—H5A···O3	0.83	1.93	2.754 (2)	172
O5—H5B···O1ⁱⁱⁱ	0.81	2.01	2.814 (2)	170

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

Acknowledgements

This project was sponsored by the K. C. Wong Magna Fund of Ningbo University and supported by the Expert Project for Key Basic Research of the Ministry of Science and Technology of China (grant No. 2003CCA00800), the Zhejiang Provincial Natural Science Foundation (grant No. Z203067) and the Ningbo Municipal Natural Science Foundation (grant No. 2006 A610061).

References

Delgado, L. C., Fabelo, O., Pasàn, J., Delgado, F. S., Lloret, F., Julve, M. & Ruiz-Pérez, C. (2007). Inorg. Chem. 46, 7458–7465. Web of Science PubMed Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Liu, Y. Y., Ma, J. F., Yang, J., Ma, J. C. & Su, Z. M. (2008). CrystEngComm, 10, 894–904. Web of Science CrossRef CAS Google Scholar
McKee, V. & Najafpour, M. M. (2007). Acta Cryst. E63, o741–o743. CSD CrossRef IUCr Journals Google Scholar
Najafpour, M. M., Hołyńska, M. & Lis, T. (2008). Acta Cryst. E64, o985. Web of Science CSD CrossRef IUCr Journals Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar