Benzene-1,3,5-triol at 105 K.

The structure of the title compound, C(6)H(6)O(3), has been redetermined at low temperature [room-temperature structure: Maartmann-Moe (1965 ▶). Acta Cryst. 19, 155-157]. The mol-ecule is planar with approximate D(3h) point symmetry, yet it crystallizes in the chiral ortho-rhom-bic space group P2(1)2(1)2(1) with a three-dimensional hydrogen-bonding network containing infinite O-H⋯O-H⋯O-H chains.

Related literature

For the structure at room temperature, see: Maartmann-Moe (1965 ▶). For the hydrate structure, see: Wallwork & Powell (1957 ▶).

Experimental

Crystal data

C6H6O3

M = 126.11

Orthorhombic,

a = 4.7778 (2) Å

b = 9.3581 (4) Å

c = 12.4433 (6) Å

V = 556.35 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 105 (2) K

0.20 × 0.08 × 0.05 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.916, T max = 0.997

6178 measured reflections

743 independent reflections

728 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.081

S = 1.13

743 reflections

91 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808030638/bi2305sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808030638/bi2305Isup2.hkl

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

Enhanced figure: interactive version of Fig. 1

C6H6O3	F(000) = 264
Mr = 126.11	Dx = 1.506 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4652 reflections
a = 4.7778 (2) Å	θ = 2.7–27.1°
b = 9.3581 (4) Å	µ = 0.12 mm−1
c = 12.4433 (6) Å	T = 105 K
V = 556.35 (4) Å3	Needle, colourless
Z = 4	0.20 × 0.08 × 0.05 mm

Siemens SMART CCD diffractometer	743 independent reflections
Radiation source: fine-focus sealed tube	728 reflections with I > 2σ(I)
graphite	Rint = 0.014
ω scans	θmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.916, Tmax = 0.997	k = −11→11
6178 measured reflections	l = −15→15

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)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.054P)2 + 0.1017P] where P = (Fo2 + 2Fc2)/3
743 reflections	(Δ/σ)max < 0.001
91 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.20 e Å−3

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. Data were collected by measuring three sets of exposures with the detector set at 2θ = 29°, crystal-to-detector distance 5.00 cm. Refinement of F2 against ALL reflections.

	x	y	z	Uiso*/Ueq
O1	0.2140 (2)	0.48267 (10)	0.56722 (8)	0.0160 (3)
H1	0.189 (5)	0.560 (2)	0.5979 (15)	0.024*
O2	0.8083 (3)	0.25657 (10)	0.31075 (8)	0.0167 (3)
H2	0.760 (5)	0.189 (2)	0.3432 (14)	0.025*
O3	0.7415 (2)	0.76483 (10)	0.32139 (8)	0.0160 (3)
H3	0.884 (5)	0.7549 (19)	0.2792 (16)	0.024*
C1	0.3967 (3)	0.49437 (14)	0.48167 (11)	0.0135 (3)
C2	0.5004 (3)	0.36808 (13)	0.43819 (11)	0.0141 (3)
H21	0.4423	0.2779	0.4652	0.017*
C3	0.6913 (3)	0.37730 (13)	0.35413 (10)	0.0135 (3)
C4	0.7758 (3)	0.50800 (15)	0.31202 (11)	0.0150 (3)
H41	0.9054	0.5126	0.2542	0.018*
C5	0.6651 (3)	0.63152 (13)	0.35689 (10)	0.0134 (3)
C6	0.4732 (3)	0.62700 (13)	0.44129 (11)	0.0137 (3)
H61	0.3970	0.7124	0.4704	0.016*

	U11	U22	U33	U12	U13	U23
O1	0.0199 (5)	0.0107 (5)	0.0173 (5)	−0.0003 (4)	0.0057 (4)	−0.0006 (3)
O2	0.0217 (5)	0.0090 (5)	0.0194 (5)	0.0017 (4)	0.0058 (4)	0.0000 (4)
O3	0.0209 (6)	0.0093 (5)	0.0177 (5)	−0.0015 (4)	0.0054 (5)	0.0009 (3)
C1	0.0127 (6)	0.0142 (6)	0.0136 (6)	−0.0006 (6)	−0.0006 (5)	−0.0004 (5)
C2	0.0152 (6)	0.0109 (6)	0.0161 (6)	−0.0009 (5)	−0.0003 (6)	0.0017 (5)
C3	0.0142 (6)	0.0108 (6)	0.0154 (6)	0.0014 (6)	−0.0013 (6)	−0.0012 (5)
C4	0.0158 (6)	0.0141 (6)	0.0150 (6)	0.0000 (5)	0.0032 (5)	0.0003 (5)
C5	0.0152 (7)	0.0104 (6)	0.0145 (6)	−0.0017 (6)	−0.0014 (6)	0.0012 (5)
C6	0.0151 (6)	0.0110 (6)	0.0152 (6)	0.0005 (5)	0.0008 (6)	−0.0020 (5)

O1—C1	1.3808 (17)	C2—C3	1.3905 (19)
O1—H1	0.83 (2)	C2—H21	0.9500
O2—C3	1.3712 (16)	C3—C4	1.3905 (18)
O2—H2	0.79 (2)	C4—C5	1.3884 (19)
O3—C5	1.3730 (15)	C4—H41	0.9500
O3—H3	0.86 (2)	C5—C6	1.3945 (19)
C1—C6	1.3881 (17)	C6—H61	0.9500
C1—C2	1.3910 (18)
C1—O1—H1	112.2 (14)	C2—C3—C4	121.90 (12)
C3—O2—H2	109.9 (14)	C5—C4—C3	118.05 (12)
C5—O3—H3	107.9 (12)	C5—C4—H41	121.0
O1—C1—C6	121.10 (11)	C3—C4—H41	121.0
O1—C1—C2	117.24 (11)	O3—C5—C4	121.72 (12)
C6—C1—C2	121.67 (12)	O3—C5—C6	116.41 (11)
C3—C2—C1	118.27 (12)	C4—C5—C6	121.87 (12)
C3—C2—H21	120.9	C1—C6—C5	118.22 (12)
C1—C2—H21	120.9	C1—C6—H61	120.9
O2—C3—C2	120.83 (12)	C5—C6—H61	120.9
O2—C3—C4	117.26 (12)
O1—C1—C2—C3	−178.06 (12)	O1—C1—C6—C5	178.09 (12)
C6—C1—C2—C3	1.8 (2)	C2—C1—C6—C5	−1.8 (2)
C1—C2—C3—O2	177.59 (12)	O3—C5—C6—C1	−178.14 (12)
C1—C2—C3—C4	−1.1 (2)	C4—C5—C6—C1	1.0 (2)
O2—C3—C4—C5	−178.32 (13)	H1—O1—C1—C6	−13.0 (16)
C2—C3—C4—C5	0.4 (2)	H2—O2—C3—C2	−4.3 (16)
C3—C4—C5—O3	178.75 (13)	H3—O3—C5—C4	−10.8 (14)
C3—C4—C5—C6	−0.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3i	0.83 (2)	1.94 (2)	2.7426 (13)	164 (2)
O2—H2···O1ii	0.79 (2)	1.97 (2)	2.7424 (14)	169 (2)
O3—H3···O2iii	0.86 (2)	1.85 (2)	2.7086 (16)	173.3 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3i	0.83 (2)	1.94 (2)	2.7426 (13)	164 (2)
O2—H2⋯O1ii	0.79 (2)	1.97 (2)	2.7424 (14)	169 (2)
O3—H3⋯O2iii	0.86 (2)	1.85 (2)	2.7086 (16)	173.3 (17)

Symmetry codes: (i) ; (ii) ; (iii) .