Benzene-1,3-diacetic acid.

Mol-ecules of the title compound, C(10)H(10)O(4), are connected through O-H⋯O hydrogen-bonding inter-actions 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 = 194.18

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.121

S = 1.06

1094 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802504X/bt2762sup1.cif

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

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

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

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 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

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.

	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*

	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)

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

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

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) .