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Acta Crystallogr Sect E Struct Rep Online. 2008 October 1; 64(Pt 10): o2023.
Published online 2008 September 27. doi:  10.1107/S1600536808030638
PMCID: PMC2959261

Benzene-1,3,5-triol at 105 K

Abstract

The structure of the title compound, C6H6O3, has been redetermined at low temperature [room-temperature structure: Maartmann-Moe (1965 [triangle]). Acta Cryst. 19, 155–157]. The mol­ecule is planar with approximate D 3h point symmetry, yet it crystallizes in the chiral ortho­rhom­bic space group P212121 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 [triangle]). For the hydrate structure, see: Wallwork & Powell (1957 [triangle]).

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Object name is e-64-o2023-scheme1.jpg

Experimental

Crystal data

  • C6H6O3
  • M r = 126.11
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2023-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The purchase of the diffractometer was made possible through support from the Research Council of Norway (NFR).

supplementary crystallographic information

Comment

The structure of the benzene-1,3,5-triol, commonly known as phloroglucinol, is shown in Fig. 1. The molecule is essentially planar, with D3h point symmetry, having only small out-of-plane rotations for the hydroxyl groups. Rather than forming a layer-like structure, a folded molecular aggregation pattern is observed in the crystal (Fig. 2) giving a three-dimensional hydrogen-bonding pattern. The three hydrogen bonds listed in Table 1 form an infinite zigzag chain along the b axis as shown in Fig. 3. The agreement with the original structure determination (Maartmann-Moe, 1965) is generally good, but with some significant changes in the hydrogen bonding geometries.

Benzene-1,3,5-triol has also been crystallized as a dihydrate, which is divided into layers with water molecules as connectors (Wallwork & Powell, 1957).

Experimental

The title compound was obtained from Fluka. Crystals were grown by diffusion of hexane into 30 µl of a solution containing 2.1 mg benzene-1,3,5-triol and 1.3 mg triazin in 3-methyl-2-butanone.

Refinement

Positional parameters were refined for hydroxylic H atoms, while H atoms bonded to C were positioned with idealized geometry and C—H distance 0.95 Å. Uiso values were 1.5Ueq(O) and 1.2Ueq(C). In the absence of significant anomalous scattering effects, 1585 Friedel pairs were merged.

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are shown at the 50% probability level and H-atoms are shown as spheres of arbitrary size.
Fig. 2.
Molecular packing and unit cell of the title compound viewed along the b axis. Hydrogen bonding is indicated by dashed lines, H-atoms bonded to C have been omitted for clarity. The three different hydroxylic O atoms have been depicted in different colours. ...
Fig. 3.
Detail of the hydrogen bonding pattern showing infinite hydrogen-bonded chains.

Crystal data

C6H6O3F(000) = 264
Mr = 126.11Dx = 1.506 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4652 reflections
a = 4.7778 (2) Åθ = 2.7–27.1°
b = 9.3581 (4) ŵ = 0.12 mm1
c = 12.4433 (6) ÅT = 105 K
V = 556.35 (4) Å3Needle, colourless
Z = 40.20 × 0.08 × 0.05 mm

Data collection

Siemens SMART CCD diffractometer743 independent reflections
Radiation source: fine-focus sealed tube728 reflections with I > 2σ(I)
graphiteRint = 0.014
ω scansθmax = 27.1°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −6→6
Tmin = 0.916, Tmax = 0.997k = −11→11
6178 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.054P)2 + 0.1017P] where P = (Fo2 + 2Fc2)/3
743 reflections(Δ/σ)max < 0.001
91 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = −0.20 e Å3

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. 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O10.2140 (2)0.48267 (10)0.56722 (8)0.0160 (3)
H10.189 (5)0.560 (2)0.5979 (15)0.024*
O20.8083 (3)0.25657 (10)0.31075 (8)0.0167 (3)
H20.760 (5)0.189 (2)0.3432 (14)0.025*
O30.7415 (2)0.76483 (10)0.32139 (8)0.0160 (3)
H30.884 (5)0.7549 (19)0.2792 (16)0.024*
C10.3967 (3)0.49437 (14)0.48167 (11)0.0135 (3)
C20.5004 (3)0.36808 (13)0.43819 (11)0.0141 (3)
H210.44230.27790.46520.017*
C30.6913 (3)0.37730 (13)0.35413 (10)0.0135 (3)
C40.7758 (3)0.50800 (15)0.31202 (11)0.0150 (3)
H410.90540.51260.25420.018*
C50.6651 (3)0.63152 (13)0.35689 (10)0.0134 (3)
C60.4732 (3)0.62700 (13)0.44129 (11)0.0137 (3)
H610.39700.71240.47040.016*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0199 (5)0.0107 (5)0.0173 (5)−0.0003 (4)0.0057 (4)−0.0006 (3)
O20.0217 (5)0.0090 (5)0.0194 (5)0.0017 (4)0.0058 (4)0.0000 (4)
O30.0209 (6)0.0093 (5)0.0177 (5)−0.0015 (4)0.0054 (5)0.0009 (3)
C10.0127 (6)0.0142 (6)0.0136 (6)−0.0006 (6)−0.0006 (5)−0.0004 (5)
C20.0152 (6)0.0109 (6)0.0161 (6)−0.0009 (5)−0.0003 (6)0.0017 (5)
C30.0142 (6)0.0108 (6)0.0154 (6)0.0014 (6)−0.0013 (6)−0.0012 (5)
C40.0158 (6)0.0141 (6)0.0150 (6)0.0000 (5)0.0032 (5)0.0003 (5)
C50.0152 (7)0.0104 (6)0.0145 (6)−0.0017 (6)−0.0014 (6)0.0012 (5)
C60.0151 (6)0.0110 (6)0.0152 (6)0.0005 (5)0.0008 (6)−0.0020 (5)

Geometric parameters (Å, °)

O1—C11.3808 (17)C2—C31.3905 (19)
O1—H10.83 (2)C2—H210.9500
O2—C31.3712 (16)C3—C41.3905 (18)
O2—H20.79 (2)C4—C51.3884 (19)
O3—C51.3730 (15)C4—H410.9500
O3—H30.86 (2)C5—C61.3945 (19)
C1—C61.3881 (17)C6—H610.9500
C1—C21.3910 (18)
C1—O1—H1112.2 (14)C2—C3—C4121.90 (12)
C3—O2—H2109.9 (14)C5—C4—C3118.05 (12)
C5—O3—H3107.9 (12)C5—C4—H41121.0
O1—C1—C6121.10 (11)C3—C4—H41121.0
O1—C1—C2117.24 (11)O3—C5—C4121.72 (12)
C6—C1—C2121.67 (12)O3—C5—C6116.41 (11)
C3—C2—C1118.27 (12)C4—C5—C6121.87 (12)
C3—C2—H21120.9C1—C6—C5118.22 (12)
C1—C2—H21120.9C1—C6—H61120.9
O2—C3—C2120.83 (12)C5—C6—H61120.9
O2—C3—C4117.26 (12)
O1—C1—C2—C3−178.06 (12)O1—C1—C6—C5178.09 (12)
C6—C1—C2—C31.8 (2)C2—C1—C6—C5−1.8 (2)
C1—C2—C3—O2177.59 (12)O3—C5—C6—C1−178.14 (12)
C1—C2—C3—C4−1.1 (2)C4—C5—C6—C11.0 (2)
O2—C3—C4—C5−178.32 (13)H1—O1—C1—C6−13.0 (16)
C2—C3—C4—C50.4 (2)H2—O2—C3—C2−4.3 (16)
C3—C4—C5—O3178.75 (13)H3—O3—C5—C4−10.8 (14)
C3—C4—C5—C6−0.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.83 (2)1.94 (2)2.7426 (13)164 (2)
O2—H2···O1ii0.79 (2)1.97 (2)2.7424 (14)169 (2)
O3—H3···O2iii0.86 (2)1.85 (2)2.7086 (16)173.3 (17)

Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) x+1/2, −y+1/2, −z+1; (iii) −x+2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2305).

References

  • Bruker (1998). SMART Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2001). SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Maartmann-Moe, K. (1965). Acta Cryst.19, 155–157.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wallwork, S. C. & Powell, H. M. (1957). Acta Cryst.10, 48–52.

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