Benzene-1,3-diacetic acid

Zhu, M.

doi:10.1107/S160053680802504X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1719

doi:10.1107/S160053680802504X

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Benzene-1,3-diacetic acid

Mei Zhu ^a ^*

^aDepartment of Biology, College of Chemistry and Biology, Beihua University, Jilin City 132013, People's Republic of China
^*Correspondence e-mail: jlsmz@126.com

(Received 1 August 2008; accepted 4 August 2008; online 6 August 2008)

Molecules of the title compound, C₁₀H₁₀O₄, are connected through O—H⋯O hydrogen-bonding interactions into chains running along the c axis.

Related literature

For related literature, see Huo et al. (2004 ); Ma et al. (2003 ).

Experimental

Crystal data

C₁₀H₁₀O₄
M_r = 194.18
Orthorhombic, P 2₁ 2₁ 2₁
a = 4.9506 (9) Å
b = 10.0840 (17) Å
c = 18.576 (3) Å
V = 927.3 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 (2) K
0.31 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 )T_min = 0.965, T_max = 0.981
5569 measured reflections
1094 independent reflections
970 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.121
S = 1.06
1094 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O1ⁱ	0.82	1.87	2.665 (3)	165
O2—H2⋯O3ⁱⁱ	0.82	1.87	2.673 (3)	165
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, z.

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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. DOI: 10.1107/S160053680802504X/bt2762sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802504X/bt2762Isup2.hkl

checkCIF report

Comment top

The self-organization of small molecules with O—H···O and other weak intermolecular interactions is used to create one-, two-, and three-dimensional networks in crystalline solids (Huo et al., 2004). Recently, aromatic di- or poly(carboxylic acids) have been investigated in the area of solid state and material science (Ma et al., 2003). The title compound was synthesized from benzene-1,3-diacetic acid. In the crystal, molecules of the title compound are connected through O—H···O H-bonding interactions to chains running along the c-axis.

Related literature top

For related literature, see Huo et al. (2004); Ma et al. (2003).

Experimental top

A hot aqueous solution of benzene-1,3-diacetic acid (1 mmol) was stirred until the white solids were dissolved. The clear solution was allowed to cool to room temperature and evaporated in air for 5 days. Then, colourless crystals of the title compound were obtained.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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. The structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Benzene-1,3-diacetic acid top

Crystal data top

C₁₀H₁₀O₄	F(000) = 408
M_r = 194.18	D_x = 1.391 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1094 reflections
a = 4.9506 (9) Å	θ = 1.1–26.1°
b = 10.0840 (17) Å	µ = 0.11 mm⁻¹
c = 18.576 (3) Å	T = 293 K
V = 927.3 (3) Å³	Block, colorless
Z = 4	0.31 × 0.21 × 0.19 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1094 independent reflections
Radiation source: fine-focus sealed tube	970 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 26.1°, θ_min = 2.2°
Absorption correction: multi-scan (SAINT; Bruker, 1998)	h = −6→5
T_min = 0.965, T_max = 0.981	k = −10→12
5569 measured reflections	l = −22→22

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0719P)² + 0.1185P] where P = (F_o² + 2F_c²)/3
1094 reflections	(Δ/σ)_max = 0.001
127 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.12 e Å⁻³

Crystal data top

C₁₀H₁₀O₄	V = 927.3 (3) Å³
M_r = 194.18	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 4.9506 (9) Å	µ = 0.11 mm⁻¹
b = 10.0840 (17) Å	T = 293 K
c = 18.576 (3) Å	0.31 × 0.21 × 0.19 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1094 independent reflections
Absorption correction: multi-scan (SAINT; Bruker, 1998)	970 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.981	R_int = 0.020
5569 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.121	H-atom parameters constrained
S = 1.06	Δρ_max = 0.21 e Å⁻³
1094 reflections	Δρ_min = −0.12 e Å⁻³
127 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	0.6445 (5)	1.3039 (2)	0.89747 (14)	0.0773 (7)
O4	0.4524 (5)	0.53787 (19)	0.85467 (15)	0.0880 (8)
H4A	0.5318	0.4677	0.8616	0.132*
O2	1.0157 (5)	1.3432 (2)	0.83572 (13)	0.0805 (7)
H2	0.9320	1.4113	0.8265	0.121*
O3	0.8315 (5)	0.5825 (3)	0.79804 (15)	0.0910 (8)
C8	0.7293 (5)	0.9447 (2)	0.85307 (14)	0.0504 (6)
H8	0.8198	0.9542	0.8095	0.060*
C1	0.8739 (6)	1.2698 (2)	0.87529 (15)	0.0524 (7)
C7	0.5408 (5)	0.8441 (2)	0.86027 (14)	0.0503 (6)
C3	0.7872 (6)	1.0315 (2)	0.90849 (15)	0.0542 (7)
C2	0.9924 (6)	1.1399 (3)	0.89799 (18)	0.0668 (8)
H2A	1.0900	1.1526	0.9427	0.080*
H2B	1.1216	1.1116	0.8619	0.080*
C10	0.5972 (6)	0.6126 (3)	0.81796 (15)	0.0557 (7)
C9	0.4895 (7)	0.7476 (3)	0.79898 (15)	0.0626 (8)
H9A	0.2971	0.7418	0.7897	0.075*
H9B	0.5771	0.7794	0.7556	0.075*
C6	0.4047 (6)	0.8332 (3)	0.92448 (16)	0.0642 (8)
H6	0.2743	0.7676	0.9300	0.077*
C5	0.4588 (7)	0.9185 (3)	0.98098 (17)	0.0751 (10)
H5	0.3660	0.9098	1.0242	0.090*
C4	0.6514 (7)	1.0169 (3)	0.97298 (15)	0.0669 (8)
H4	0.6895	1.0735	1.0112	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0676 (14)	0.0528 (11)	0.1114 (17)	0.0114 (11)	0.0163 (14)	0.0152 (11)
O4	0.0761 (15)	0.0466 (10)	0.141 (2)	0.0002 (11)	0.0161 (15)	0.0274 (13)
O2	0.0756 (14)	0.0531 (11)	0.1130 (17)	0.0032 (12)	0.0200 (13)	0.0085 (12)
O3	0.0769 (16)	0.0728 (15)	0.123 (2)	0.0130 (14)	0.0221 (15)	0.0279 (14)
C8	0.0480 (13)	0.0394 (12)	0.0637 (15)	0.0030 (11)	0.0000 (12)	0.0093 (11)
C1	0.0520 (14)	0.0367 (12)	0.0684 (16)	−0.0057 (12)	−0.0130 (14)	−0.0069 (12)
C7	0.0445 (13)	0.0378 (12)	0.0686 (16)	0.0017 (10)	−0.0042 (13)	0.0142 (11)
C3	0.0507 (15)	0.0343 (11)	0.0775 (17)	0.0080 (11)	−0.0106 (13)	0.0041 (12)
C2	0.0531 (16)	0.0452 (14)	0.102 (2)	−0.0005 (13)	−0.0150 (17)	−0.0032 (15)
C10	0.0578 (16)	0.0420 (13)	0.0674 (16)	−0.0084 (13)	−0.0140 (14)	0.0039 (12)
C9	0.0645 (17)	0.0489 (15)	0.0745 (17)	−0.0043 (14)	−0.0209 (16)	0.0103 (13)
C6	0.0559 (17)	0.0465 (14)	0.090 (2)	0.0036 (14)	0.0103 (16)	0.0181 (14)
C5	0.090 (2)	0.0599 (18)	0.0756 (19)	0.0226 (19)	0.0233 (18)	0.0163 (15)
C4	0.083 (2)	0.0498 (15)	0.0682 (17)	0.0193 (17)	−0.0042 (16)	−0.0023 (14)

Geometric parameters (Å, º) top

O1—C1	1.256 (4)	C3—C4	1.382 (4)
O4—C10	1.244 (4)	C3—C2	1.505 (4)
O4—H4A	0.8200	C2—H2A	0.9700
O2—C1	1.258 (3)	C2—H2B	0.9700
O2—H2	0.8200	C10—C9	1.503 (4)
O3—C10	1.255 (4)	C9—H9A	0.9700
C8—C3	1.381 (3)	C9—H9B	0.9700
C8—C7	1.385 (3)	C6—C5	1.383 (4)
C8—H8	0.9300	C6—H6	0.9300
C1—C2	1.496 (4)	C5—C4	1.384 (5)
C7—C6	1.375 (4)	C5—H5	0.9300
C7—C9	1.519 (4)	C4—H4	0.9300

C10—O4—H4A	109.5	H2A—C2—H2B	107.6
C1—O2—H2	109.5	O4—C10—O3	123.2 (3)
C3—C8—C7	122.1 (2)	O4—C10—C9	118.2 (3)
C3—C8—H8	118.9	O3—C10—C9	118.6 (3)
C7—C8—H8	118.9	C10—C9—C7	110.2 (2)
O1—C1—O2	122.3 (3)	C10—C9—H9A	109.6
O1—C1—C2	120.2 (3)	C7—C9—H9A	109.6
O2—C1—C2	117.5 (3)	C10—C9—H9B	109.6
C6—C7—C8	118.2 (3)	C7—C9—H9B	109.6
C6—C7—C9	121.1 (3)	H9A—C9—H9B	108.1
C8—C7—C9	120.6 (2)	C7—C6—C5	120.9 (3)
C8—C3—C4	118.5 (3)	C7—C6—H6	119.5
C8—C3—C2	120.2 (3)	C5—C6—H6	119.5
C4—C3—C2	121.2 (3)	C6—C5—C4	119.9 (3)
C1—C2—C3	114.1 (2)	C6—C5—H5	120.1
C1—C2—H2A	108.7	C4—C5—H5	120.1
C3—C2—H2A	108.7	C3—C4—C5	120.3 (3)
C1—C2—H2B	108.7	C3—C4—H4	119.8
C3—C2—H2B	108.7	C5—C4—H4	119.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1ⁱ	0.82	1.87	2.665 (3)	165
O2—H2···O3ⁱⁱ	0.82	1.87	2.673 (3)	165

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₀O₄
M_r	194.18
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	4.9506 (9), 10.0840 (17), 18.576 (3)
V (Å³)	927.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.31 × 0.21 × 0.19

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SAINT; Bruker, 1998)
T_min, T_max	0.965, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	5569, 1094, 970
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.618

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.121, 1.06
No. of reflections	1094
No. of parameters	127
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.12

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), 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
O4—H4A···O1ⁱ	0.82	1.87	2.665 (3)	164.5
O2—H2···O3ⁱⁱ	0.82	1.87	2.673 (3)	164.8

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

Acknowledgements

The author thanks the Beihua University for supporting this work.

References

Bruker (1998). SMART SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Huo, L.-H., Gao, S., Zhao, H., Zain, S. M. & Ng, S. W. (2004). Acta Cryst. E60, o1394–o1396. Web of Science CSD CrossRef IUCr Journals Google Scholar
Ma, J.-F., Yang, J., Zheng, G.-L., Li, L. & Liu, J.-F. (2003). Inorg. Chem. 42, 7531–7534. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar