Benzene-1,3-diacetic acid

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

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.045
• wR factor = 0.122
• Data-to-parameter ratio = 8.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C10
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.07

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.07
           From the CIF: _reflns_number_total               1094
           Count of symmetry unique reflns         1104
           Completeness (_total/calc)             99.09%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. 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.

Related literature

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

S2. 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.

S3. 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).

Computing details

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

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

Crystal data

C10H10O4	F(000) = 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 = 1.1–26.1°
b = 10.0840 (17) Å	µ = 0.11 mm^−1
c = 18.576 (3) Å	T = 293 K
V = 927.3 (3) Å^3	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)
Graphite monochromator	Rint = 0.020
ϕ and ω scans	θmax = 26.1°, θmin = 2.2°
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 F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0719P)^2 + 0.1185P] where P = (Fo^2 + 2Fc^2)/3
1094 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.12 e Å^−3

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)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1^i	0.82	1.87	2.665 (3)	165
O2—H2···O3^ii	0.82	1.87	2.673 (3)	165

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