Benzene-1,3-diacetic acid

Abstract

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,

• a = 4.9506 (9) Å

• b = 10.0840 (17) Å

• c = 18.576 (3) Å

• V = 927.3 (3) ų

• 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[F ² > 2σ(F ²)] = 0.044

• wR(F ²) = 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

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.

Supplementary Material

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

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) ; (ii) .

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

In the absence of anomalous scatterers Friedel pairs (714) were merged. H atoms were generated geometrically and refined as riding atoms with O—H= 0.82Å, C_aromatic—H= 0.93Å C_methylene—H= 0.97Å and U_iso(H)= 1.2 times U_eq(C) or U_iso(H)= 1.5 times U_eq(O).

Figures

Fig. 1.

The structure of the title compound with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C10H10O4	F000 = 408
Mr = 194.18	Dx = 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 = 1.1–26.1º
b = 10.0840 (17) Å	µ = 0.11 mm−1
c = 18.576 (3) Å	T = 293 (2) K
V = 927.3 (3) Å3	Block, colorless
Z = 4	0.31 × 0.21 × 0.19 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer	1094 independent reflections
Radiation source: fine-focus sealed tube	970 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 293(2) K	θmax = 26.1º
φ and ω scans	θmin = 2.2º
Absorption correction: multi-scan(SAINT; Bruker, 1998)	h = −6→5
Tmin = 0.965, Tmax = 0.981	k = −10→12
5569 measured reflections	l = −22→22

Refinement

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.0719P)2 + 0.1185P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
1094 reflections	Δρmax = 0.21 e Å−3
127 parameters	Δρmin = −0.12 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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.